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

Participants

Reaction Steps

Add methanesulfonyl chloride (1.12 mol, 128.8 g) drop wise to a solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.74 mol, 150 g) and triethylamine (1.5 mol, 151.6 g) in dichloromethane (1 L) at 0° C. Upon complete addition, warm the reaction mixture to room temperature and stir for 16 h. Dilute the reaction mixture with dichloromethane, wash with saturated sodium bicarbonate solution and water. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (192 g, 92%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 1.78-1.85 (m, 2H), 1.93-1.98 (m, 2H), 3.03 (s, 3H), 3.26-3.32 (m, 2H), 3.68-3.71 (m, 2H), 4.85-4.90 (m 1H).

Provenance & Evidence