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A Novel Asymmetric Route to 4-Phenyl-1, 2, 3, 4-Tetrahydroisoquinolines}{\b\lang2057\langfe1036\langnp2057 \par }{\b\f4\lang2057\langfe1036\langnp2057 \par }{\f4\lang2057\langfe1036\langnp2057 Nicolas Philippe, Vincent Levacher*, Georges Dupas, Guy Qu\'e9guiner and \par Jean Bourguignon \par }\pard \qc \li426\ri-51\sl480\slmult0\widctlpar\nooverflow\faroman\rin-51\lin426\itap0 {\b\f4\lang2057\langfe1036\langnp2057 \par \par }\pard \qj \li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 {\b\f4\lang2057\langfe1036\langnp2057 \tab General section.}{\f4\lang2057\langfe1036\langnp2057 Tetrahydrofuran (THF) was distilled from sodium/benzophenone ketyl under N}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 . Other solvents were used without further purification. Flash column chr omatography was performed either with a 32-63 mesh silica gel or alumina oxide neutral (50-180 }{\f3 \'6d}{\f4\lang2057\langfe1036\langnp2057 m). 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202000000100b0013e0102000e00200000001100040000004320202000000100b001210102001000040000001200200000004320202000000100c90112010200 1100200000001300040000004320202000000100e201210102001200040000001400200000004320202000000100e2013e0102001300200000000e0004000000 0000000000000100010001002424242407000000fc020100000000000000040000002d010600040000002d0101000300000000000000000000000000000000000000000000000000000000000000000000000000}}}}}{\f4\lang2057\langfe1036\langnp2057 \par }\pard \qj \li0\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin0\itap0 {\b\f4\lang2057\langfe1036\langnp2057 \tab \par \tab }{\b\i\f4\lang2057\langfe1036\langnp2057 N}{\b\f4\lang2057\langfe1036\langnp2057 -[(R)-2-hydroxy-1-phenylethyl]-1,4-dihydroisoquinolin-3-one (1).}{\f4\lang2057\langfe1036\langnp2057 To a solution of HBr (3.96 g, 49.3 mmol) in dry EtOH (30 mL) was added portionwise isochroman-3-one (2 g, 13.7 mmol) at 0\'b0C. After being stirred at room temperature for 48 h, EtOH was evapora ted to dryness affording 3.1 g of ethyl 2-(bromomethyl)phenylacetate }{\b\f4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 as a brown oil. The crude product was taken on to the next step without further purification: }{ \f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR (200 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.45-7.15 (m, 4H), 4.62 (s, 2H), 4.17 (q,}{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 7.1 Hz, 2H), 3.81 (s, 2H), 1.25 (t, }{ \i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 7.1 Hz, 3H). To a stirred solution of ethyl 2-(bromomethyl)phenylacetate }{ \b\f4\lang2057\langfe1036\langnp2057 2 }{\f4\lang2057\langfe1036\langnp2057 (3 g, 16.7 mmol) in EtOH (20 mL) was added (R)-(-)-2-amino-2-phenylethanol (1.8 g, 13.1 mmol) and K}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 CO}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 (4 g, 30 mmol). The resulting solution was sti rred at room temperature for 48 h and stirred for an additional 24 h at reflux. The reaction mixture was quenched with water (50 mL) and extracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (3 x 30 mL). The combined organic phases were dried (MgSO}{\f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 ) and evaporated. Flash chromatography (Alumina; eluent: EtOAc/EtOH 95/5) afforded 2.76 g (62%) of }{\b\f4\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 as a white amorphous solid. mp 102\'b0C; [}{\f3 \'61}{\f4\lang2057\langfe1036\langnp2057 ]}{ \f4\up6\lang2057\langfe1036\langnp2057 19}{\f4\dn4\lang2057\langfe1036\langnp2057 D}{\f4\lang2057\langfe1036\langnp2057 = -39.2 (CHCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 , c=0.503), IR (neat) 3300, 2884, 1647 cm} {\f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; }{\f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR (400 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{ \f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.33-7.16 (m, 8H), 7.00 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{ \f4\lang2057\langfe1036\langnp2057 7.5 Hz, 1H), 5.89 (dd,}{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 8.7 and 5.4 Hz, 1H), 4.40 (d, }{ \i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 15.5 Hz, 1H), 4.23 (dd,}{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 11.7 and 5.4 Hz, 1H), 4.14 (dd, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{ \f4\lang2057\langfe1036\langnp2057 11.7 and 8.7 Hz, 1H), 4.11 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 15.5 Hz, 1H), 3.68 (s, 2H), 2.61 (brs, 1H); }{\f4\up6\lang2057\langfe1036\langnp2057 13}{\f4\lang2057\langfe1036\langnp2057 C NMR (100 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{ \f4\lang2057\langfe1036\langnp2057 171.0, 136.5, 132.2, 131.9, 128.8, 127.8, 127.5, 127.0, 126.6, 125.1, 61.9, 58.5, 46.8, 38.3; Anal. Calcd for C}{\f4\dn4\lang2057\langfe1036\langnp2057 17}{\f4\lang2057\langfe1036\langnp2057 H}{ \f4\dn4\lang2057\langfe1036\langnp2057 17}{\f4\lang2057\langfe1036\langnp2057 NO}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 : C, 76.38; H, 6.41; N, 5.24. Found: C, 76.42; H, 6.59; N, 5.27. \par }\pard \qj \li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 {\f4\lang2057\langfe1036\langnp2057 \par }\pard \qc \li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 {\pard\plain \qc \li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 \f12\fs20\lang1036\langfe1036\cgrid\langnp1036\langfenp1036 {\object\objemb\objw1872\objh1508{\*\objclass ChemDraw.Document.4.0}{\*\objdata 0105000002000000160000004368656d447261772e446f63756d656e742e342e3000000000000000000000160000 d0cf11e0a1b11ae1000000000000000000000000000000003e000300feff0900060000000000000000000000010000000100000000000000001000000200000001000000feffffff0000000000000000ffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffff 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\li0\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin0\itap0 {\f4\lang2057\langfe1036\langnp2057 \tab }{\b\f4\lang2057\langfe1036\langnp2057 (4S}{\b\f4\up6\lang2057\langfe1036\langnp2057 *}{\b\f4\lang2057\langfe1036\langnp2057 )-}{\b\i\f4\lang2057\langfe1036\langnp2057 N}{\b\f4\lang2057\langfe1036\langnp2057 -[(R)-2-hydroxy-1-phenylethyl]-4-benzyl-1,4-dihydroisoquinolin-3-one [(4S)-3].}{\f4\lang2057\langfe1036\langnp2057 To a solution of }{\b\f4\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 (1 g, 3.74 mmol) in dry THF (40 mL) cooled to -78\'b0C was added dropwise a solution of LHMDS in THF (5.84 mL, 1.6M, 9.35 mmol) under argon. The reaction mixture was stirred at this temperature for 30 min and benzyl bromide (1.33 mL, 11.2 mmol) was added over a period of 5 min. The solution was stirred for a further 3 h. The reaction mixture was treated with a saturated solution of NH}{ \f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 Cl (40 mL) and the solution was allowed to reach room temperature. After phase separation, the aqueous phase was extracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{ \f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (3 x 40 mL). The combined organic layers were dried (MgSO}{\f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 ) and evaporated under vacuum. The diastereoisomeric excess (de>97%) was deduced by analysis of }{\f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR spectra and confirmed by HPLC analysis of the crude product. [chromatographic conditions: column C18 (250 x 4.6; 5 }{\f3 \'6d}{\f4\lang2057\langfe1036\langnp2057 m); UV detection (}{\f3 \'6c}{\f4\lang2057\langfe1036\langnp2057 =210nm); eluent: CH}{ \f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 CN/H}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 O (70/30); flow rate: 1 mL/min; temperature: 22 \'b0C; injection: 20 }{\f3 \'6d}{ \f4\lang2057\langfe1036\langnp2057 L (1 mg of sample in 20 mL of eluent)]. Purification of the crude product by flash chromatography on alumina (eluent: CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 /EtOH 9.5/0.5) afforded 1.1 g (80%) of (4S)-}{\b\f4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 : mp 97\'b0C; IR (neat) 3225, 1612 cm}{ \f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; [}{\f3 \'61}{\f4\lang2057\langfe1036\langnp2057 ]}{\f4\up6\lang2057\langfe1036\langnp2057 19}{\f4\dn4\lang2057\langfe1036\langnp2057 D}{\f4\lang2057\langfe1036\langnp2057 = -37.3 (CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 , c=0.496); }{\f4\up6\lang2057\langfe1036\langnp2057 1}{ \f4\lang2057\langfe1036\langnp2057 H NMR (300 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.39-6.90 (m, 12H), 6.75 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{ \f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 8.9 Hz, 2H), 5.69 (dd, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 7.3 and }{\i\f4\lang2057\langfe1036\langnp2057 J= }{\f4\lang2057\langfe1036\langnp2057 5.5 Hz, 1H), 4.12 (m, 2H), 3.93 (appt, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{ \i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 5.5 Hz, 1H), 3.92 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 16.0 Hz, 1H), 3.33 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 16.0 Hz, 1H), 3.24 (dd, }{\i\f4\lang2057\langfe1036\langnp2057 J}{ \f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 13.1 and }{\i\f4\lang2057\langfe1036\langnp2057 J= }{\f4\lang2057\langfe1036\langnp2057 6.6 Hz, 1H), 3.14 (dd, }{ \i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 13.1 and }{\i\f4\lang2057\langfe1036\langnp2057 J= }{\f4\lang2057\langfe1036\langnp2057 4.0 Hz, 1H); }{\f4\up6\lang2057\langfe1036\langnp2057 13}{\f4\lang2057\langfe1036\langnp2057 C NMR (75 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{\f4\lang2057\langfe1036\langnp2057 172.6, 137.1, 136.0, 134.7, 131.5, 129.5, 128.7, 128.2, 128.0 (x2), 127.6, 127.4, 126.7, 126.5, 125.0, 62.0, 59.8, 49.3, 47.2, 40.6; Anal. Calcd for C}{\f4\dn4\lang2057\langfe1036\langnp2057 24}{\f4\lang2057\langfe1036\langnp2057 H}{ \f4\dn4\lang2057\langfe1036\langnp2057 23}{\f4\lang2057\langfe1036\langnp2057 NO}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 : C, 80.64; H, 6.49; N, 3.92. Found: C, 80.42; H, 6.47; N, 3.90. \par }\pard \qj \li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 {\fs20\lang1024\langfe1024\noproof {\shp{\*\shpinst\shpleft3911\shptop830\shpright5783\shpbottom2420\shpfhdr0\shpbxcolumn\shpbxignore\shpbypara\shpbyignore\shpwr3\shpwrk0\shpfblwtxt0\shpz0\shplid1026{\sp{\sn shapeType}{\sv 1}}{\sp{\sn fFlipH}{\sv 0}}{\sp{\sn fFlipV}{\sv 0}} {\sp{\sn lTxid}{\sv 65536}}{\sp{\sn dxTextLeft}{\sv 0}}{\sp{\sn dyTextTop}{\sv 0}}{\sp{\sn dxTextRight}{\sv 0}}{\sp{\sn dyTextBottom}{\sv 0}}{\sp{\sn fFilled}{\sv 0}}{\sp{\sn lineWidth}{\sv 0}}{\sp{\sn fLine}{\sv 0}}{\sp{\sn fShadow}{\sv 0}} {\sp{\sn fLayoutInCell}{\sv 0}}{\sp{\sn fLayoutInCell}{\sv 0}}{\shptxt \pard\plain \ql \li0\ri0\widctlpar\nooverflow\faroman\rin0\lin0\itap0 \f12\fs24\lang1036\langfe1036\cgrid\langnp1036\langfenp1036 {\pard\plain \ql \li0\ri0\widctlpar\nooverflow\faroman\rin0\lin0\itap0 \f12\fs20\lang1036\langfe1036\cgrid\langnp1036\langfenp1036 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}}\dpx3911\dpy830\dpxsize1872\dpysize1590\dpfillfgcr255\dpfillfgcg255\dpfillfgcb255\dpfillbgcr255\dpfillbgcg255\dpfillbgcb255\dpfillpat0\dplinehollow}}}}{\f4\lang2057\langfe1036\langnp2057 \par }{\b\f4\lang2057\langfe1036\langnp2057 \par \par \par \par \par \tab (4S}{\b\f4\up6\lang2057\langfe1036\langnp2057 *}{\b\f4\lang2057\langfe1036\langnp2057 )-}{\b\i\f4\lang2057\langfe1036\langnp2057 N}{\b\f4\lang2057\langfe1036\langnp2057 -[(R)-2-hydroxy-1-phenylethyl]-4-deuterio-4-benzyl-1,4-dihydroisoquinolin-3-one [(4S)-3-}{\b\i\f4\lang2057\langfe1036\langnp2057 d}{\b\i\f4\dn4\lang2057\langfe1036\langnp2057 1}{\b\f4\lang2057\langfe1036\langnp2057 ]. }{\f4\lang2057\langfe1036\langnp2057 To a solution of (4S)-}{\b\f4\lang2057\langfe1036\langnp2057 3.}{\f4\lang2057\langfe1036\langnp2057 (250 mg, 0.70 mmol) in dry THF (40 mL) was added dropwise butyllithium in hexane (0.84 mL, 2.5M, 2.7 mmol) at -78\'b0 C. After stirring at this temperature for 30 min, EtOD (1 mL) was added dropwise at -78\'b0C and the solution was allowed to reach room temperature over a period of 2 hours. The reaction mixture was quenched with a saturated solution of NH}{ \f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 Cl (10 mL). After evaporation of THF, the aqueous layer was extracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (3 x 20 mL). The resulting organic phase was dried (MgSO}{\f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 ) and evaporated affording (4S)-}{ \b\f4\lang2057\langfe1036\langnp2057 3-}{\i\f4\lang2057\langfe1036\langnp2057 d}{\i\f4\dn4\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 as a pale yellow oil (}{\b\f4\lang2057\langfe1036\langnp2057 3}{ \f4\lang2057\langfe1036\langnp2057 -}{\i\f4\lang2057\langfe1036\langnp2057 d}{\i\f4\dn4\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 ./}{\b\f4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 95/5). Diastereomeric excess (de=90%) was determined par HPLC [chromatographic conditions: : column C18 (250 x 4.6; 5 }{\f3 \'6d}{\f4\lang2057\langfe1036\langnp2057 m); UV detection (}{\f3 \'6c}{\f4\lang2057\langfe1036\langnp2057 =210nm); eluent: CH}{ \f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 CN/ H}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 O (70/30); flow rate: 1 mL/min; temperature: 22 \'b0C; injection: 20 }{\f3 \'6d}{ \f4\lang2057\langfe1036\langnp2057 L (1 mg of sample in 20 mL of eluent)]. The crude product was subjected to column chromatography on alumina (eluent: CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 /EtOH 9.5/0.5) to afford (4S)-}{\b\f4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 -}{\i\f4\lang2057\langfe1036\langnp2057 d}{ \i\f4\dn4\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 in 90% yield as a white solid: mp 97\'b0C; IR (neat) 3225, 1612 cm}{\f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; }{ \f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR (300 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.39-6.90 (m, 12H), 6.75 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 8.9 Hz, 2H), 5.69 (dd, }{\i\f4\lang2057\langfe1036\langnp2057 J}{ \f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 7.3 and }{\i\f4\lang2057\langfe1036\langnp2057 J= }{\f4\lang2057\langfe1036\langnp2057 5.5 Hz, 1H), 4.12 (m, 2H), 3.93 (d, }{ \i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 16.0 Hz, 1H), 3.33 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J }{\f4\lang2057\langfe1036\langnp2057 =}{\i\f4\lang2057\langfe1036\langnp2057 }{\f4\lang2057\langfe1036\langnp2057 16.0 Hz, 1H), 3.24 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{ \f4\lang2057\langfe1036\langnp2057 13.1 Hz, 1H), 3.14 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 13.1 Hz, 1H); }{ \f4\up6\lang2057\langfe1036\langnp2057 13}{\f4\lang2057\langfe1036\langnp2057 C NMR (75 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{\f4\lang2057\langfe1036\langnp2057 17 2.6, 137.1, 136.0, 134.7, 131.5, 129.4, 128.7, 128.2, 128.0 (x2), 127.6, 127.4, 126.7, 126.5, 125.0, 62.0, 59.8, 49.3, 47.2, 40.6; Anal Calcd for C}{\f4\dn4\lang2057\langfe1036\langnp2057 24}{\f4\lang2057\langfe1036\langnp2057 H}{ \f4\dn4\lang2057\langfe1036\langnp2057 22}{\f4\lang2057\langfe1036\langnp2057 DNO}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 : C, 80.42; H/D, 6.75; N, 3.91. 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argon to a solution of sodium borohydride (4.36 g, 115 mmol) in dry THF (150 mL). After 5 min, 2-(phenylmethyl)benzoic acid (10 g, 47 mmol) was added and the mixture was stirred under reflux overnight. After cooling the solution to 0\'b0 C, methanol (40 mL) was added dropwise. The resulting mixture was stirred at room temperature for a further 30 min. Solvents were evaporated to dryne ss and 20% aqueous KOH (150 mL) was then added to the residue. The solution was stirred for 4 h at room temperature and then extracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (3 x 60 mL). The combined CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{ \f4\lang2057\langfe1036\langnp2057 layers were dried (MgSO}{\f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 ) and evaporated under vacuum. The crude product was purified by chromatography on silica gel (eluent: CH}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 ) to yield 8.4 g (90%) of }{\b\f4\lang2057\langfe1036\langnp2057 4 }{ \f4\lang2057\langfe1036\langnp2057 as a colorless oil: IR (neat) 3328, 2920 cm}{\f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; }{\f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR (200 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.50-7.40 (m, 1H), 7.35-7.10 (m, 8H), 4.65 (s, 2H), 4.10 (s, 2H), 1.6 (brs, 1H); }{ \f4\up6\lang2057\langfe1036\langnp2057 13}{\f4\lang2057\langfe1036\langnp2057 C NMR (50 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{\f4\lang2057\langfe1036\langnp2057 140.3, 136.7, 136.3, 130.3, 128.6, 128.4, 128.0, 127.7, 126.6, 126.0, 62.7, 38.2; Anal Calcd for C}{\f4\dn4\lang2057\langfe1036\langnp2057 14}{\f4\lang2057\langfe1036\langnp2057 H}{\f4\dn4\lang2057\langfe1036\langnp2057 14}{ \f4\lang2057\langfe1036\langnp2057 O: C, 84.81; H, 7.12. 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Et}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 O (150 mL) cooled to -78\'b0C was added dropwise under N}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 a solution of butyllithium in hexane (42.4 mL, 2.5 M, 105.9 mmol). The solution was stirred for 24 h at room temperature. The solution was then treated with methyl chloroformate (6.5 mL, 84.74 mmol) at -78\'b0C and stirred for 3 h at this temperature. After addition of aq 2N HCl (70 mL) and phase separation, the aqueous layer was extracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{ \f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (3 x 50 mL). The combined organic layers were dried (MgSO}{\f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 ) and the solvent evaporated under vacuum. The residue was chromatographed on a silica gel column (eluent: Et}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 O/EtOAc 3/7) affording 4.54 g (54%) of a white solid: mp 98\'b0 C; IR (neat) 2987, 2895, 2848, 1736 cm}{\f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; }{\f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR (200 MHz, CDCl}{ \f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.45-7.10 (m, 9H), 5.25 (s, 2H), 5.05 (s, 1H); }{\f4\up6\lang2057\langfe1036\langnp2057 13}{\f4\lang2057\langfe1036\langnp2057 C NMR (50 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{\f4\lang2057\langfe1036\langnp2057 171.0, 134.2, 133.9, 131.8, 128.85, 128.75, 128.1, 127.8, 127.7, 127.6, 124.8, 69.4, 51.6; Anal. Calcd for C}{\f4\dn4\lang2057\langfe1036\langnp2057 15}{\f4\lang2057\langfe1036\langnp2057 H}{\f4\dn4\lang2057\langfe1036\langnp2057 12}{ \f4\lang2057\langfe1036\langnp2057 O}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 : C, 80.34; H, 5.39. Found: C, 80.42; H, 5.46. \par \par }\pard \qc \fi567\li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 {\pard\plain \qc \fi567\li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 \f12\fs20\lang1036\langfe1036\cgrid\langnp1036\langfenp1036 {\object\objemb\objw1660\objh1808{\*\objclass ChemDraw.Document.4.0}{\*\objdata 0105000002000000160000004368656d447261772e446f63756d656e742e342e3000000000000000000000160000 d0cf11e0a1b11ae1000000000000000000000000000000003e000300feff0900060000000000000000000000010000000100000000000000001000000200000001000000feffffff0000000000000000ffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffff ffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffff 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0400000043202020000001009a010b0102001600040000001800200000004320202000000100b301fd0002001700200000001900040000004320202000000100 cc010b0102001800040000001a00200000004320202000000100cc01280102001900200000000f00040000000000000000000100010001002424242407000000 fc020100000000000000040000002d010600040000002d010100030000000000000000000000000000000000000000000000000000000000000000000000000000000000}}}}}{\f4\lang2057\langfe1036\langnp2057 \par }\pard \qj \fi567\li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 {\f4\lang2057\langfe1036\langnp2057 \par \par }\pard \qj \li0\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin0\itap0 {\f4\lang2057\langfe1036\langnp2057 \tab }{\b\i\f4\lang2057\langfe1036\langnp2057 N}{\b\f4\lang2057\langfe1036\langnp2057 -[(R)-2-hydroxy-1-phenylethyl]-4-phenyl-1,4-dihydroisoquinolin-3-one [(4R,4S)-6].}{\f4\lang2057\langfe1036\langnp2057 A solution of 4-phenylisochroman-3-one }{\b\f4\lang2057\langfe1036\langnp2057 5}{\f4\lang2057\langfe1036\langnp2057 (2 g, 8.9 mmol) and HBr (2.6 g, 32 mmol) in dry EtOH (20 mL) was stirred at room temperature for 48 h. After evaporation of EtOH under vacuum, R-(-)-2-amino-2-phenylethanol (1.35 g, 9.8 mmol) and potassium carbonate (4.9 g, 35.6 mmol) was added to the residue. After addition of EtOH (20 mL), the resulting solution was stirred for 48 h at room temperature, then for 24 h at reflux. After evaporation of EtOH, the residue was dissolved in CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2 }{ \f4\lang2057\langfe1036\langnp2057 (30 mL) and water (50 mL). After phase separation, the resulting aqueous phase was extracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (2 x 20 mL). The organic phases were dried (MgSO}{\f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 ) and the solvent evaporated under vacuum affording 3.5 g of a thick orange oil. The crude product was purified by chromatography on silica gel (eluent: CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 /EtOH 98/2) to give 1.7 g (55%) of the desired lactam (4R,4S)-}{\b\f4\lang2057\langfe1036\langnp2057 6}{\f4\lang2057\langfe1036\langnp2057 as a colorless oil. }{ \f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR spectrum analysis showed that lactam (4R,4S)-}{\b\f4\lang2057\langfe1036\langnp2057 6}{\f4\lang2057\langfe1036\langnp2057 was obtained as a 50:50 epimeric mixture. Both epimers could be analyzed by HPLC [chromatographic conditions: Chiralcel OD (250 x 4.6; 10 }{\f3 \'6d}{\f4\lang2057\langfe1036\langnp2057 m); UV detection (}{\f3 \'6c}{\f4\lang2057\langfe1036\langnp2057 =230nm); eluent: hexane / 2-propanol (90/10); flow rate: 1 mL / min; temperature: 20 \'b0C; injection: 20 }{\f3 \'6d}{\f4\lang2057\langfe1036\langnp2057 L (0.5 mg of sample in 10 mL of eluent); (R,R)-diastereoisomere: 17.73 min, (S,R)-diastereoisomere: 20.52 min]: IR (neat) 3392, 1629 cm}{\f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; }{ \f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR (300 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.55-7.02 (m, 28H), 5.79 (dd, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 8.5 and }{\i\f4\lang2057\langfe1036\langnp2057 J}{ \f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 5.2 Hz, 1H), 5.72 (appt,}{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{ \i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 6.5 Hz, 1H), 5.01 (s, 1H), 4.98 (s, 1H), 4.41 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{ \f4\lang2057\langfe1036\langnp2057 15.7 Hz, 1H), 4.23-4.05 (m, 7H); }{\f4\up6\lang2057\langfe1036\langnp2057 13}{\f4\lang2057\langfe1036\langnp2057 C NMR (50 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{\f4\lang2057\langfe1036\langnp2057 171.6, 171.55, 138.1, 137.8, 136.5, 135.4, 135.2, 132.0, 131.8, 128.55, 128.50 (x2), 128.45, 127.90 (x2), 127.75, 127.60 (x2), 127.55, 127.50, 127.2, 127.05, 127.00, 126.90, 126.60, 125.25, 61.5, 61.1, 58.4, 58.3, 53.7, 53.4, 46.5, 45.9; Anal. Calcd for C }{\f4\dn4\lang2057\langfe1036\langnp2057 23}{\f4\lang2057\langfe1036\langnp2057 H}{\f4\dn4\lang2057\langfe1036\langnp2057 21}{\f4\lang2057\langfe1036\langnp2057 NO}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 : C, 80.44; H, 6.16; N, 4.08. Found: C, 80.31; H, 6.24; N, 3.98. \par }\pard \qj \li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 {\fs20\lang1024\langfe1024\noproof {\shp{\*\shpinst\shpleft4055\shptop669\shpright5927\shpbottom2145\shpfhdr0\shpbxcolumn\shpbxignore\shpbypara\shpbyignore\shpwr3\shpwrk0\shpfblwtxt0\shpz1\shplid1027{\sp{\sn shapeType}{\sv 1}}{\sp{\sn fFlipH}{\sv 0}}{\sp{\sn fFlipV}{\sv 0}} {\sp{\sn lTxid}{\sv 131072}}{\sp{\sn dxTextLeft}{\sv 0}}{\sp{\sn dyTextTop}{\sv 0}}{\sp{\sn dxTextRight}{\sv 0}}{\sp{\sn dyTextBottom}{\sv 0}}{\sp{\sn fFilled}{\sv 0}}{\sp{\sn lineWidth}{\sv 0}}{\sp{\sn fLine}{\sv 0}}{\sp{\sn fShadow}{\sv 0}} {\sp{\sn fLayoutInCell}{\sv 0}}{\sp{\sn fLayoutInCell}{\sv 0}}{\shptxt \pard\plain \ql \li0\ri0\widctlpar\nooverflow\faroman\rin0\lin0\itap0 \f12\fs24\lang1036\langfe1036\cgrid\langnp1036\langfenp1036 {\pard\plain \ql \li0\ri0\widctlpar\nooverflow\faroman\rin0\lin0\itap0 \f12\fs20\lang1036\langfe1036\cgrid\langnp1036\langfenp1036 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-[(R)-2-hydroxy-1-phenylethyl]-4-phenyl-1,4-dihydroisoquinolin-3-one [(4S)-6].}{\f4\lang2057\langfe1036\langnp2057 To a solution of the epimeric mixtu re of compound (4R,4S)-}{\b\f4\lang2057\langfe1036\langnp2057 6}{\f4\lang2057\langfe1036\langnp2057 (200 mg, 0.58 mmol) in dry THF (8 mL) cooled to -78\'b0 C was added under argon a solution of butyllithium in hexane (0.7 mL, 2.5 M, 1.74 mmol). After stirring at this temperature for 30 min, a saturated aqueous solution of NH}{\f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 Cl (10 mL) was added dropwise and the solution was stirred at -78\'b0C for a further 3 h. The solution was allowed to reach room temperature. The aqueous phase was extracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{ \f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (3 x 20 mL) and the combined organic layers were dried (MgSO}{\f4\dn4\lang2057\langfe1036\langnp2057 4}{ \f4\lang2057\langfe1036\langnp2057 ) and concentrated. Diastereomeric excess (97%) was measured by HPLC analysis (chromatographic conditions are described above) and by analysis of the }{\f4\up6\lang2057\langfe1036\langnp2057 1}{ \f4\lang2057\langfe1036\langnp2057 H NMR spectrum of the crude product. The crude product was then chromatographed on silica gel (eluent: CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 /EtOH 98/2) yielding 184 mg (92%) of the desired product (4S)-}{\b\f4\lang2057\langfe1036\langnp2057 6}{\f4\lang2057\langfe1036\langnp2057 : mp 99\'b0C; [}{\f3 \'61}{ \f4\lang2057\langfe1036\langnp2057 ]}{\f4\up6\lang2057\langfe1036\langnp2057 19}{\f4\dn4\lang2057\langfe1036\langnp2057 D}{\f4\lang2057\langfe1036\langnp2057 = -45 (CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 , c=0.98); IR (neat) 3423, 3029, 2946, 1628 cm}{\f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; }{\f4\up6\lang2057\langfe1036\langnp2057 1}{ \f4\lang2057\langfe1036\langnp2057 H NMR (200 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.35-7.05 (m, 14H), 5.72 (appt,}{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 6.5 Hz, 1H), 4.98 (s, 1H), 4.23-4.15 (m, 3H), 4.08 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{ \i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 16.0 Hz, 1H), 2.65 (brs, 1H); }{\f4\up6\lang2057\langfe1036\langnp2057 13}{\f4\lang2057\langfe1036\langnp2057 C NMR (50 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{ \f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{\f4\lang2057\langfe1036\langnp2057 172.1, 137.8, 136.3, 135.3, 132.1, 128.8, 128.7, 128.2, 128.0, 127.9, 127.8, 127.7, 127.3, 127.1, 125.4, 62.0, 59.6, 53.8, 47.3; Anal. Calcd for C}{ \f4\dn4\lang2057\langfe1036\langnp2057 23}{\f4\lang2057\langfe1036\langnp2057 H}{\f4\dn4\lang2057\langfe1036\langnp2057 21}{\f4\lang2057\langfe1036\langnp2057 NO}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 : C, 80.44; H, 6.16; N, 4.08. Found: C, 80.62; H, 6.41; N, 4.01. \par }\pard \qc \li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 {\pard\plain \qc \li426\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin426\itap0 \f12\fs20\lang1036\langfe1036\cgrid\langnp1036\langfenp1036 {\object\objemb\objw1728\objh1402{\*\objclass ChemDraw.Document.4.0}{\*\objdata 0105000002000000160000004368656d447261772e446f63756d656e742e342e3000000000000000000000160000 d0cf11e0a1b11ae1000000000000000000000000000000003e000300feff0900060000000000000000000000010000000100000000000000001000000200000001000000feffffff0000000000000000ffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffff ffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffff 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\li0\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin0\itap0 {\f4\lang2057\langfe1036\langnp2057 \tab }{\b\f4\lang2057\langfe1036\langnp2057 (4S*)-}{\b\i\f4\lang2057\langfe1036\langnp2057 N}{ \b\f4\lang2057\langfe1036\langnp2057 -[(R)-2-hydroxy-1-phenylethyl]-4-phenyl-1,2,3,4-tetrahydroisoquinoline [(4S)-7]. }{\f4\lang2057\langfe1036\langnp2057 To a solution of sodium borohydride (540 mg, 14.6 mmol) in dry THF (30 mL) was added dropwise under argon a solution of iodine (740 mg, 5.8 mmol) in THF (20 mL) at 0\'b0C. The mixture was kept for additional 5 min, compound (4S)-}{\b\f4\lang2057\langfe1036\langnp2057 6}{\f4\lang2057\langfe1036\langnp2057 was then added and the mixture was stirred under reflux overnight. After cooling the solution to 0\'b0C, methanol (15 mL) was added dropwise and the resulting mixture was stirred at room temperature for a further 30 min. Solvents were evaporated to dryness and 20% aqueous NaOH (60 mL) was then added to the residue. The solution was stirred for 4 h at room temperature and then e xtracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (3 x 40 mL). The organic layer was washed with 1N aqueous HCl (10 mL). The resulting acidic aqueous phase was washed with Et}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 O (3x10 mL). After neutralization with 2M NaOH (pH=6-7), the aqueous phase was extracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{ \f4\lang2057\langfe1036\langnp2057 (3x20 mL). The combined CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 layers were dried (MgSO}{ \f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 ) and evaporated under vacuum to yield 1.32 g (69%) of (4S)-}{\b\f4\lang2057\langfe1036\langnp2057 7 }{\f4\lang2057\langfe1036\langnp2057 (de>97%) as a thick colorless oil: IR (neat) 3041, 2928 cm}{\f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; }{\f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR (200 MHz, CDCl}{ \f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.41-7.02 (m, 13H), 6.89 (d,}{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{ \i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 8.0 Hz, 1H), 4.27 (appt, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{ \f4\lang2057\langfe1036\langnp2057 4.85 Hz, 1H), 3.90-3.75 (m, 4H), 3.66-3.52 (m, 1H), 2.95 (dd, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 11.5 and 5.5 Hz, 1H), 2.79 (dd, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 11.5 and 4.5 Hz, 1H); }{\f4\up6\lang2057\langfe1036\langnp2057 13}{ \f4\lang2057\langfe1036\langnp2057 C NMR (60 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{\f4\lang2057\langfe1036\langnp2057 145.2, 136.6, 135.4, 135.2, 129.7, 128.8, 128.7, 128.3, 128.2, 127.9, 126.5, 126.3 (x2), 126.1, 69.1, 60.4, 54.3, 52.6, 45.7; Anal. Calcd for C}{\f4\dn4\lang2057\langfe1036\langnp2057 23}{\f4\lang2057\langfe1036\langnp2057 H}{ \f4\dn4\lang2057\langfe1036\langnp2057 23}{\f4\lang2057\langfe1036\langnp2057 NO: C, 83.86; H, 7.04; N, 4.25. 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200000000f00040000004320202000000100b301900102000e000400000010002000000043202020000001009a019e0102000f00200000001100040000004320 20200000010081019001020010000400000012002000000043202020000001008101730102001100200000000b00040000000000000000000100010001002424242407000000fc020100000000000000040000002d010600040000002d0101000300000000000000000000000000000000000000}{\*\bkmkend OLE_LINK1} }}}}{\f4\lang2057\langfe1036\langnp2057 \par }\pard \qj \li0\ri-51\sl480\slmult0\widctlpar\tx993\nooverflow\faroman\rin-51\lin0\itap0 {\f4\lang2057\langfe1036\langnp2057 \tab \par }{\b\f4 (4S*)-4-phenyl-1,2,3,4-tetrahydroisoquinoline (8).}{\f4 }{\f4\lang2057\langfe1036\langnp2057 To a solution of compound (4S)-}{\b\f4\lang2057\langfe1036\langnp2057 7}{\f4\lang2057\langfe1036\langnp2057 (400 mg, 1.2 mmol) in MeOH (10 mL) was added 20 % Pd(OH)}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (150 mg) and 1N aqueous HCl (1 mL). The resulting solution was stirred for 12 h under a hydrogen atmosphere. The catalyst was filtrated through Celite and washed with MeOH (2 x 15 mL). After evaporation of the solvent, the residue was dissolved in CH}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (20 mL). The CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl }{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 phase was extracted with 1N aqueous HCl (30 mL) and the resulting aqueous phase was washed with Et}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{ \f4\lang2057\langfe1036\langnp2057 O (2 x 15 mL) to extract 2-phenylethanol. The aqueous layer was made basic with 2N aqueous NaOH (pH=6-7) and extracted with CH}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 Cl}{ \f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\lang2057\langfe1036\langnp2057 (2 x 30 mL). Drying (MgSO}{\f4\dn4\lang2057\langfe1036\langnp2057 4}{\f4\lang2057\langfe1036\langnp2057 ) and evaporation of the solvent yielded 165 mg (65%) of }{ \b\f4\lang2057\langfe1036\langnp2057 8}{\f4\lang2057\langfe1036\langnp2057 : IR (neat) 3306, 2937 cm}{\f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; }{\f4\up6\lang2057\langfe1036\langnp2057 1}{ \f4\lang2057\langfe1036\langnp2057 H NMR (200 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.34-7.08 (m, 8H), 6.90 (d,}{\i\f4\lang2057\langfe1036\langnp2057 J}{ \f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 7.0 Hz, 1H), 4.15 (m, 3H), 3.42 (dd, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{ \i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 13.0 Hz and 5.4 Hz, 1H), 3.16 (dd, 13.0 Hz and 6.5 Hz, 1H), 1.83 (brs, 1H); }{\f4\up6\lang2057\langfe1036\langnp2057 13}{\f4\lang2057\langfe1036\langnp2057 C NMR (50 MHz, CDCl}{ \f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{\f4\lang2057\langfe1036\langnp2057 140.1, 135.5, 129.2, 129.0, 128.9, 127.9 (x2), 127.6, 127.2, 126.4, 47.8, 44.5, 41.6; Anal. Calcd for C}{ \f4\dn4\lang2057\langfe1036\langnp2057 15}{\f4\lang2057\langfe1036\langnp2057 H}{\f4\dn4\lang2057\langfe1036\langnp2057 15}{\f4\lang2057\langfe1036\langnp2057 N: C, 86.08; H, 7.22; N, 6.69. 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4348454d4452415720342e304d4943524f534f465420574f303030333130313034353030000000001200432020200000010061013d0102000200200000000600 040000004320202000000100610128010200010020000000030004000000432020200000010074011d0102000200040000000400200000004320202000000000 870128010300030020000000050004000000070004000000432020200000000087013d0103000400040000000600200000000a00040000004320202000000100 74014801020005002000000001000400000043202020000002009a011d0102000400040000000800040000004e20202000000000ac0128010300070004000000 0900040000000c00040000004320202000000200ac013d0102000800040000000a000400000043202020000000009a0148010400090004000000050004000000 0b00040002000d000400040043202020000000009a01650103000e00200000001200040000000a00040010004320202000000300bf011d010100080004000000 48202020000000008a01570101000a00040020004320202000000100b301730102000b00200000000f00040000004320202000000100b301900102000e000400 000010002000000043202020000001009a019e0102000f0020000000110004000000432020200000010081019001020010000400000012002000000043202020 000001008101730102001100200000000b00040000000000000000000100010001002424242407000000fc020100000000000000040000002d010700040000002d0101000300000000000000000000000000000000000000}}}}}{\f4\lang2057\langfe1036\langnp2057 \par }\pard \qj \li0\ri-51\sl480\slmult0\widctlpar\nooverflow\faroman\rin-51\lin0\itap0 {\b\f4\lang2057\langfe1036\langnp2057 \par }\pard \qj \fi567\li0\ri-51\sl480\slmult0\widctlpar\nooverflow\faroman\rin-51\lin0\itap0 {\b\f4\lang2057\langfe1036\langnp2057 (4S*)-}{\b\i\f4\lang2057\langfe1036\langnp2057 N}{\b\f4\lang2057\langfe1036\langnp2057 -methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline (9).}{\f4\lang2057\langfe1036\langnp2057 A solution of }{\b\f4\lang2057\langfe1036\langnp2057 8}{\f4\lang2057\langfe1036\langnp2057 (50 mg, 0.24 mmol) and paraformaldehyde (373 mg, 11.95 mmol) in MeOH (10 mL) was stirred at reflux for 1 h. After cooling to room temperature, 20% Pd(OH)}{\f4\dn4\lang2057\langfe1036\langnp2057 2}{\f4\up6\lang2057\langfe1036\langnp2057 }{\f4\lang2057\langfe1036\langnp2057 (140 mg) was added and the solution was stirred under hydrogen atmosphere for 16 h. The catalyst was filtered though a plug of Celite and washed with MeOH (2 x 20 mL). Solvent was evaporated under vacuum affording 533 mg (95%) of compound }{ \b\f4\lang2057\langfe1036\langnp2057 9}{\f4\lang2057\langfe1036\langnp2057 (ee>97%). The enantiomeric excess was determined by chiral HPLC using the following chromatographic conditions. [Column: Chiracel OD (250 x 4.6; 10 }{\f3 \'6d}{ \f4\lang2057\langfe1036\langnp2057 m); UV detection (}{\f3 \'6c}{\f4\lang2057\langfe1036\langnp2057 =230nm); Eluent: hexane / 2-propanol (90/10); Flow rate: 1 mL / min; Temperature: 22 \'b0C; Injection: 20 }{\f3 \'6d}{\f4\lang2057\langfe1036\langnp2057 L (0.5 mg of sample in 10 mL of hexane); (S)-enantiomere: 4.3 min, (R) enantiomere: 5.5 min]; [}{\f3 \'61}{\f4\lang2057\langfe1036\langnp2057 ]}{\f4\up6\lang2057\langfe1036\langnp2057 22}{\f4\dn4\lang2057\langfe1036\langnp2057 D}{ \f4\lang2057\langfe1036\langnp2057 = 17.2 (MeOH, c= 0.80) [lit.}{\f4\up6\lang2057\langfe1036\langnp2057 15 }{\f4\lang2057\langfe1036\langnp2057 [}{\f3 \'61}{\f4\lang2057\langfe1036\langnp2057 ]}{\f4\up6\lang2057\langfe1036\langnp2057 24}{ \f4\dn4\lang2057\langfe1036\langnp2057 D }{\f4\lang2057\langfe1036\langnp2057 = 16.7 (100% e.e.) (MeOH, c=0.72)]; IR (neat) 3059, 2937 cm}{\f4\up6\lang2057\langfe1036\langnp2057 -1}{\f4\lang2057\langfe1036\langnp2057 ; }{ \f4\up6\lang2057\langfe1036\langnp2057 1}{\f4\lang2057\langfe1036\langnp2057 H NMR (200 MHz, CDCl}{\f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64}{\f4\lang2057\langfe1036\langnp2057 7.39-7.04 (m, 8H), 6.93 (d,}{ \i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 7.55 Hz, 1H), 4.36 (appt, }{\i\f4\lang2057\langfe1036\langnp2057 J}{ \f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 7.0 Hz, 1H), 3.80 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 15.0 Hz, 1H), 3.62 (d, }{\i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 15.0 Hz, 1H), 3.10 (dd, }{ \i\f4\lang2057\langfe1036\langnp2057 J}{\f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 11.5 and 5.0 Hz, 1H), 2.61 (dd, }{\i\f4\lang2057\langfe1036\langnp2057 J}{ \f4\lang2057\langfe1036\langnp2057 }{\i\f4\lang2057\langfe1036\langnp2057 = }{\f4\lang2057\langfe1036\langnp2057 11.5 and 8.5 Hz, 1H), 2.43 (s, 3H); }{\f4\up6\lang2057\langfe1036\langnp2057 13}{\f4\lang2057\langfe1036\langnp2057 C NMR (50 MHz, CDCl}{ \f4\dn4\lang2057\langfe1036\langnp2057 3}{\f4\lang2057\langfe1036\langnp2057 ) }{\f3 \'64\'20}{\f4\lang2057\langfe1036\langnp2057 144.9, 137.0, 135.1, 129.3, 129.0, 128.3, 126.4, 126.2, 126.1, 125.9, 61.8, 58.5, 46.0, 45.9. Anal. Calcd for C}{ \f4\dn4\lang2057\langfe1036\langnp2057 16}{\f4\lang2057\langfe1036\langnp2057 H}{\f4\dn4\lang2057\langfe1036\langnp2057 17}{\f4\lang2057\langfe1036\langnp2057 N: C, 86.05; H, 7.67; N, 6.27. Found: C, 86.20; H, 7.65; N, 6.40. \par }\pard \qj \li426\ri-51\sl480\slmult0\widctlpar\nooverflow\faroman\rin-51\lin426\itap0 {\lang2057\langfe1036\langnp2057 \par \par \par \par \par \par \par \par \par \par \par \par \par \par }\pard \qj \li0\ri-51\sl480\slmult0\widctlpar\nooverflow\faroman\rin-51\lin0\itap0 {\lang2057\langfe1036\langnp2057 \par }}