(2S,4S)-tert-butyl 4-azido-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate → tert-butyl (2S,4S)-4-amino-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate
Reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+]=[N-])[CH2:10][C@H:9]1[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>O1CCOCC1.[Pd]>[C:1]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]Participants
4
Procedure
To a solution of (2S,4S)-1-Boc-4-azido[(dimethylamino)carbonyl]pyrrolidine (9 g, 32 mmol) prepared in Step B in dioxane (30 mL) was added dropwise Pd/C (900 mg). The reaction mixture was stirred under hydrogen condition for 24 h, filtered through Celite, and concentrated in vacuo to give the title compound as an oil (8.1 g, 98.5%).