(2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-azido-2-hydroxyheptanamide → (2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-amino-2-hydroxyheptanamide
Reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][C:11](=[O:22])[C@@H:12]([OH:21])[C@@H:13]([N:18]=[N+]=[N-])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=2[O:2]1>[C].[Pd].CO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([NH:10][C:11](=[O:22])[C@@H:12]([OH:21])[C@@H:13]([NH2:18])[CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=2[O:2]1Participants
4
Procedure
To 30 ml of a methanol solution containing 395 mg (1.29 mmol) of (2S,3S)-N-[(3,4-methylenedioxy)phenyl]-3-azido-2-hydroxyheptanamide was added 40 mg of 5% palladium carbon, and the resulting mixture was stirred under hydrogen atmosphere for 18 hours. Insoluble materials were filtered off, and the filtrate was distilled under reduced pressure to obtain 344 mg (Yield: 95%) of the title compound.