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

Participants

Reaction Steps

To a stirred solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (25.55 g, 123 mmol) in CH2Cl2 (250 ml), cooled to 0° C., is slowly added Et3N (18.95 ml, 135.4 mmol) followed by methane sulfonyl chloride (9.569 ml, 123.14 mmol) and DMAP (152 mg, 1.23 mmol). The mixture is stirred at room temperature overnight. The suspension is diluted with CH2Cl2 and the phases are separated. The aqueous phase is re-extracted 3× with CH2Cl2. The combined organic layers are washed with brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. Upon concentration, the desired compound precipitates and is collected by filtration to afford, after drying in HV, the title compound as a colorless solid.

Provenance & Evidence