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

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (40 g, 0.20 moles) in dichloromethane (800 mL) was added triethylamine (83.1 mL, 0.60 moles). The reaction was cooled to 0° C. Methanesulfonyl chloride (23.1 mL, 0.30 moles) was added slowly over 15 minutes and the reaction was stirred at 0° C. for 30 minutes and then at room temperature for 16 hours. The reaction was quenched with H2O (500 mL) and the layers were cut. The organic layer was washed with H2O (2×500 mL), 1N HCl (3×500 mL) and H2O (1×500 mL). The organic layer was dried over Na2SO4 (40 g) and concentrated under reduced pressure. Ethyl acetate (50 mL) was added to the oil, followed by 350 mL of hexanes. After 3 hours, the solid was filtered and dried in a vacuum oven to afford 44.42 g (80.0%) of 4-(methanesulfonyloxy)-piperidine-1-carboxylic acid tert-butyl ester as a pale yellow solid, mp 84-86° C. 1H-NMR (400 MHz, CDCl3): δ 4.90-4.86 (m, 1H), 3.74-3.67 (m, 2H), 3.32-3.27 (m, 2H), 3.04 (s, 3H), 2.00-1.93 (m, 2H), 1.86-1.77 (m, 2H), 1.46 (s, 9H). HRMS (ESI) Calcd. for C11H21NO5S, 279.1140 (M+). Found: 279.1141. Anal. Calcd. for C11H21NO5S, C, 47.29; H, 7.58; N, 5.01; S, 11.48. Found: C, 47.49; H, 7.52; N, 5.06; S, 11.61.

Provenance & Evidence