tert-Butyl 4-((2-methoxy-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate → tert-Butyl 4-((5-amino-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate
Reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][C:4]=1[CH2:5][O:6][CH2:7][C:8]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1>CO.[Pd]>[NH2:31][C:28]1[CH:29]=[CH:30][C:3]([O:2][CH3:1])=[C:4]([CH:27]=1)[CH2:5][O:6][CH2:7][C:8]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1Participants
4
Procedure
tert-Butyl 4-((2-methoxy-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (110 mg, 0.24 mmol) in methanol (3 mL) was flushed with nitrogen, and treated with palladium (10% on charcoal, 11.0 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated to afford 96.0 mg (94%). 1H-NMR (CDCl3, 500 MHz) δ 7.33-7.38 (m, 4H), 7.22-7.25 (m, 1H), 6.62 (d, J=8.5 Hz, 1H), 6.51 (dd, J=5.8, 2.7 Hz, 1H), 6.29 (d, J=2.8 Hz, 1H), 4.37 (s, 2H), 3.70-3.74 (m, 2H), 3.43 (s, 3H), 3.42 (s, 2H), 3.03-3.07 (m, 2H), 2.15-2.18 (m, 2H), 1.88-1.93 (m, 2H), 1.43 (s, 9H). Mass spec.: 427.25 (MH)+.