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

Participants

Reaction Steps

To a solution of N-Boc-4-hydroxypiperidine (22; 25 g, 124 mmol) and Et3N (20.7 mL) in CH2Cl2 (100 mL) was added a solution of methanesulfonyl chloride 23 in CH2Cl2 (20 mL) dropwise in an ice-water bath. The mixture was stirred at room temperature for 18 h. It was then diluted with 100 mL of CH2Cl2 and washed successively with saturated aqueous Na2CO3 (50 mL) and brine (50 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to afford tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate 24 (45 g, crude yield: >100%). This material was then used in the next step without further purification.

Provenance & Evidence