C1(COC([NH:11][C@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH2:19][C:20]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])[C:13]2=[O:27])=O)C=CC=CC=1.C(O)C.C([O-])=O.[NH4+]>[Pd].C1COCC1>[NH2:11][C@H:12]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH2:19][C:20]([N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)=[O:21])[C:13]1=[O:27]To a 30° C. mixture of 1-[((3S)-3-[(phenylmethoxy)carbonyl]amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidine (20 g, 54 mmol), ethanol (100 mL), THF (100 mL) and wet 10% Pd/C (4 g) was added ammonium formate (5.1 g, 81 mmol) over 45 min. After stirring for 3 h, the reaction was cooled to room temperature and filtered. The filtrate was concentrated, taken up in TBME (150 mL) and filtered again. The filtrate was concentrated in vacuo to provide 12.3 g (95%) of (S)-1-[(3-amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidine.
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