(S)-1,1,1-Trifluoro-3-(7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-propan-2-ol → (S)-3-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-1,1,1-trifluoro-propan-2-ol
Reaction equation
[F:1][C:2]([F:21])([F:20])[C@@H:3]([OH:19])[CH2:4][N:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1>CO.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:8]2[CH2:7][CH2:6][N:5]([CH2:4][C@H:3]([OH:19])[C:2]([F:21])([F:1])[F:20])[CH2:11][CH2:10][C:9]=2[CH:12]=1Participants
4
Procedure
(S)-1,1,1-Trifluoro-3-(7-nitro-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-propan-2-ol (582 mg, 1.91 mmol, 1.0 eq) was placed in methanol (20 mL) and 10% palladium on carbon (58 mg) was added. The reaction was hydrogenated at 25 psi for 30 minutes. The mixture was then filtered through celite and concentrated under reduced pressure to obtain (S)-3-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-1,1,1-trifluoro-propan-2-ol as a green amorphous solid (525 mg, 100%). 1H-NMR (CDCl3, 400 MHz) δ 6.90 (d, 1H, J=8.2 Hz), 6.53-6.39 (m, 2H), 4.49-4.35 (m, 1H), 4.12-3.93 (m, 1H), 3.63-3.47 (m, 2H), 2.96-2.75 (m, 6H), 2.75-2.60 (m, 4H).