Methanesulfonyl chloride → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (4.50 g, 22.4 mmol, 1.0 eq) and TEA (11.3 g, 5.0 eq) in DCM (30.0 mL) at 0° C. was added MsCl (5.10 g, 44.5 mmol, 2.0 eq) in DCM (10.0 mL) dropwise. The resulting mixture was stirred at 0° C. for 30 min and then warmed to room temperature with stirring for 3 hr. After being quenched with water and extracted with ethyl acetate, the organic layers were combined, washed with brine, dried over MgSO4, filtered, and evaporated to afford the crude product, which was purified via silica gel chromatography eluting with EtOAc/petroleum ether (1:5) to afford tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (4.8 g, 77% yield) as pale yellow solid. LCMS (ESI) m/z: 224.1 [M-56+H+].

Provenance & Evidence