tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate → tert-butyl (1R,3R,4S)-4-amino-3-(methoxymethyl)cyclohexylcarbamate

Participants

Reaction Steps

A solution of (1R,3R,4S)-(4-benzyloxycarbonylamino-3-methoxymethylcyclohexyl)carbamic acid tert-butyl ester (1.24 g) was dissolved in MeOH (20 mL) and the resultant solution was charged with 20 wt % Pd(OH)2/C (300 mg) before being evacuated and purged with hydrogen. The reaction was stirred under 1 atm of H2 for 3 h and then filtered through celite with EtOAc washings. The filtrate was concentrated in vacuo to provide (1R,3R,4S)-(4-amino-3-methoxymethyl-cyclohexyl)-carbamic acid tert-butyl ester (815 mg). MS found: (M+H)+=259.2.

Provenance & Evidence