cis-4-Azidomethyl-1-tert-butoxycarbonyl-3-methoxypiperidine → tert-Butyl (3S,4R)-4-(aminomethyl)-3-methoxypiperidine-1-carboxylate
Reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][C@H:6]1[O:18][CH3:19])=[N+]=[N-]>CO.[OH-].[C+4].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[NH2:1][CH2:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7][C@H:6]1[O:18][CH3:19]Participants
4
Procedure
To a solution of cis-4-azidomethyl-1-tert-butoxycarbonyl-3-methoxypiperidine (1.5 g) in methanol (50 ml) was added 20% palladium carbon hydroxide (0.6 g), and the resulting mixture was stirred at room temperature under hydrogen atmosphere for 2 hr. 20% Palladium carbon hydroxide was filtered off and the solvent was evaporated under reduced pressure to give 1.2 g of cis-4-aminomethyl-1-tert-butoxycarbonyl-3-methoxypiperidine.