Methanesulfonyl chloride → 1-Methyl-2-oxo-3-piperidinyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (0.8 ml., 0.01 mole) was added dropwise to a stirred solution of 1-methyl-2-oxo-3-piperidinol (1.29 g, 0.01 mole) and 4-dimethylaminopyridine (2.44 g., 0.02 mole), in 50 ml. methylene chloride at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 15 min. and at 25° C. for 2.5 hours. The reaction mixture was then washed with 50 ml. saturated aqueous sodium chloride solution containing 6.8 ml. of 6N aqueous hydrochloric acid solution, dried over anhydrous sodium sulfate and concentrated in vacuo to a thick oil of the title compound (1.8 g., 87% yield). NMR (CDCl3): 1.6-2.37 (c, 4H); 2.96 (s, 3H); 3.1-3.4 (c) and 3.24 (s) (total 5H); and 4.9 (m, 1H)ppm.

Provenance & Evidence