trans-1-Benzyl-4-(4-methoxyphenyl)piperidin-3-ol → (+/-) trans-4-(4-Methoxyphenyl)-piperidin-3-ol
반응식
C([N:8]1[CH2:13][CH2:12][C@@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@H:10]([OH:22])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C@@H:11]2[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]2[OH:22])=[CH:19][CH:18]=1참가 물질
4
실험 절차
To a solution of (±)-rel-(3S,4S)-1-benzyl-4-(4-methoxyphenyl)piperidin-3-ol (7 g, 23.5 mmol) in methanol (100 mL) was added 10% Pd/C (3.76 g) and the reaction mixture was stirred overnight under a hydrogen atmosphere (balloon pressure). The catalyst was removed by filtrathou through Celite and the solvent was evaporated under reduced pressure to give (±)-rel-(3S,4S)-4-(4-methoxyphenyl)piperidin-3-ol (4.8 g, 89% yield). LCMS (method F) RT 1.485 (61.5% AP) m/z 207.8 (M+H+), 1.536 (29.7% AP), m/z 207.8 (M+H+); 1H NMR (DMSO-d6) δ 7.133 (d, J=7, 2H), 6.83 (d, J=7, 2H), 4.31 (br s, 1H), 3.7 (s, 3H), 3.02 (m, 1H), 2.86 (d, J=12, 1H), 2.45 (m, 1H), 2.22-2.39 (m, 2H), 1.62-1.61 (m, 1H), 1.610-1.46 (m, 1H).