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

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Reaction Steps

To a solution of 1-boc-4-hydroxypiperidine (32.2 g, 0.160 mol) in DCM (400 mL) was added TEA (26.8 mL, 0.192 mol), methanesulfonyl chloride (13.6 mL, 0.176 mol), DMAP (0.20 g, 0.0016 mol) at 0° C. under nitrogen atmosphere. The resulting mixture was slowly warmed to rt and stirred at the same temperature overnight. The mixture was washed with sat. aq. NaHCO3 (3×80 mL), brine (2×80 mL), and dried over anhydrous sodium sulfate. The filtrate was concentrated to give crude 4-methanesulfonyloxypiperidine-1-carboxylic acid tert-butyl ester as a white solid, 44.7 g (yield: 100%). 1H-NMR (CDCl3, 400 MHz): δ 1.47 (s, 9H), 1.80-1.85 (m, 2H), 1.95-1.99 (m, 2H), 3.05 (s, 3H), 3.28-3.34 (m, 2H), 3.68-3.74 (m, 2H), 4.89 (m, 1H) ppm. The crude product was used in the next step without further purification.

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