Triethylamine → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Participants

Reaction Steps

Triethylamine (1.4 ml, 10 mmol) was added to a stirred solution of tert-butyl 4-hydroxy-1-piperidine-carboxylate (2.0 g, 9.94 mmol) in dichloromethane (40 ml) at −17° C. under nitrogen. Methanesulfonyl chloride (0.85 ml, 11 mmol) was added dropwise and the mixture allowed to warm up to room temperature overnight. The reaction mixture was diluted with dichloromethane (50 ml) and water (100 ml) was added. The organic layer was separated and the aqueous phase was re-extracted with dichloromethane (2×50 ml). The combined organic layers were dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with 50% ethyl acetate in iso hexanes to give tert-butyl 4-methanesulfonyloxy-piperidine-1-carboxylate as a colourless oil (2.47 g, 89%),

Provenance & Evidence