Water → 1-Tert-butoxycarbonyl-4-(3-methanesulfonyloxypropoxy)piperidine

Participants

Reaction Steps

To a solution of 4-(3-hydroxypropyloxy)-N-t-butyloxycarbonylpiperidine (3.82 g) in ethyl acetate (40 ml) were added triethylamine (4.1 ml) and methanesulfonyl chloride (1.37 ml) with stirring under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture were added water (50 ml) and ethyl acetate (50 ml) with stirring. The organic layer was separated, washed twice with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 ml) eluting with a mixture of n-hexane and ethyl acetate (1:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give 4-[3-(methanesulfonyloxy)propyloxy]-N-t-butyloxycarbonylpiperidine (3.77 g).

Provenance & Evidence