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

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-hydroxypiperidine-1-carboxylate 5-1 (21.650 g, 107.57 mmol) was dissolved in 200 mL CH2Cl2. N,N,N-Triethylamine (17.991 mL, 129.08 mmol) was added and the solution was cooled to 0° C. A solution of methanesulfonyl chloride (9.991 mL, 129.08 mmol) in 50 mL CH2Cl2 was then added dropwise. The solution was allowed to warm to room temperature. After 3.5 hours, 100 mL H2O was added and the solution was stirred for 0.5 hour. The organic layer was separated, washed with 0.5N HCl and saturated NaHCO3 (aq), dried (Na2SO4), filtered, and concentrated to afford tert-butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate 5-2 as an off white solid. 1H NMR (CDCl3) δ 4.89 (m, 1H), 3.75-3.67 (m, 2H), 3.35-3.26 (m, 2H), 3.04 (s, 3H), 2.05-1.94 (m, 2H), 1.87-1.79 (m, 2H), 1.46 (s, 9H).

Provenance & Evidence