Nitrogen → tert-Butyl 4-amino-3,3-difluoropiperidine-1-carboxylate

Reaction equation

N#N.C([NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C:12]1([F:25])[F:24])C1C=CC=CC=1>CO.[Pd]>[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][C:12]1([F:25])[F:24]

Participants

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), tert-butyl 4-(benzylamino)-3,3-difluoropiperidine-1-carboxylate (0.186 g, 0.57 mmol) was dissolved in MeOH (5 mL) and wet Pd/C 10% (50 mg) was added. The flask was purged with H2 gas and the reaction mixture stirred under an H2 atmosphere for 2 h at rt. The reaction mixture was filtered over celite and the cake was washed with MeOH and EA. The filtrate was concentrated under reduced pressure to give tert-butyl 4-amino-3,3-difluoropiperidine-1-carboxylate as a colorless oil. LC-MS-conditions 08: tR=0.49 min; [M-CH3+H]+=222.32.