Methanol → (2S)-2-(4-bromophenyl)-4-[(1R)-1-phenylethyl]morpholine

반응식

B.O1CCCC1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[CH2:19][N:18]([C@@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[C:17](=O)[CH2:16][O:15]2)=[CH:10][CH:9]=1.CO>O1CCCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C@@H:14]2[O:15][CH2:16][CH2:17][N:18]([C@@H:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH3:21])[CH2:19]2)=[CH:12][CH:13]=1

참가 물질

실험 절차

A borane-tetrahydrofuran complex (1.0M solution in tetrahydrofuran, 510 ml, 510 mm) was added to the ice-cooled solution of (6S)-6-(4-bromophenyl)-4-((1R)-1-phenyethyl)-morpholin-3-one (70.2 g) in tetrahydrofuran (500 ml) over 45 minutes and the solution was stirred at the same temperature for one hour and room temperature for 30 minutes. After careful addition of methanol (60 ml) to the ice-cooled solution, the solvent was removed under reduced pressure and the residue in methanol (750 ml) and 1M aqueous sodium hydroxide (280 ml) was stirred at 80° C. for one hour with addition of 1M aqueous sodium hydroxide (70 ml) in every 15 minutes. The solvent was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. Removal of the solvent yielded (2S)-2-(4-bromophenyl)-4-((1R)-1-phenylethyl)morpholine (65.0 g, 96.3% yield, 2 steps) as white crystals.