C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][N:19]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH3:20])[CH2:14][CH2:13]1)=O)C1C=CC=CC=1>[Pd].C(O)C>[NH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][N:19]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH3:20])[CH2:14][CH2:13]1A mixture of tert-butyl trans-4-[N-[4-(N-benzyloxycarbonylamino)cyclohexylmethyl]-N-methylamino]piperidine-1-carboxylate (4.5 g), Pd-C (0.43 g) and ethanol (300 ml) was stirred vigorously for 24 hours under a hydrogen atmosphere. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The precipitated crystals were collected by filtration. The crystals were washed with diethyl ether to obtain tert-butyl trans-4-[N-(4-aminocyclohexylmethyl)-N-methylamino]piperidine-1-carboxylate (2.80 g) as colorless crystals.
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