3-Nitrobenzaldehyde → tert-Butyl (1R*,4R*)-4-(3-nitrobenzylamino)cyclohexylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl N-(4-aminocyclohexyl)carbamate (25 g, 117 mmol, 1.0 eq) and 3-nitrobenzaldehyde (18 g, 117 mmol, 1.0 eq) in MeOH (500 mL) was added NaBH(OAc)3 (50 g, 234 mmol, 2.0 eq) by portions. Then the resulting mixture was stirred overnight at 30° C. LC-MS indicated complete conversion. The solvent was removed under vacuum and the residue was purified by column chromatography (DCM:MeOH=15:1) to provide tert-butyl N-(4-[(3-nitrobenzyl)amino]cyclohexyl)carbamate (33 g, 83%) as a yellow solid.

Provenance & Evidence