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

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (550 mg, 2.5 mmol) and DMAP (296 mg, 2.5 mmol) in dichloromethane (15 mL) cooled to 0° C. by ice/water bath was added methanesulfonylchloride (189 μL, 2.5 mmol) and the resulting mixture stirred for 10 min at 0° C. and then for an additional hour at RT. The mixture was quenched with ice water and extracted with ethyl acetate (2×30 mL). The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under vacuum. The residue oil was purified via silica gel preparative plates (3×1000 mM) eluting with 50% ethyl acetate in hexane to afford the title compound (555 mg, 89%). ESI-MS calculated for C11H21NO5S: Exact Mass: 279.11. Found 302.13 (MNa)+.

Provenance & Evidence