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

Participants

Reaction Steps

A solution of tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamate (1.8 g) in N,N-dimethylformamide (15 mL)was treated sequentially with iodomethane (50 mL) and Ag2O (5.52 g), and the mixture was stirred at rt overnight. The mixture was filtered through Celite and the solids were washed with ethyl acetate. The combined filtrates were washed sequentially with water and brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 1:3 v/v ethyl acetate-hexane, to provide tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(methoxymethyl)cyclohexylcarbamate as a colorless gum (1.78 g). MS found: (M+H)+=393.

Provenance & Evidence