Triethylamine → (S)-1-((Benzyloxy)carbonyl)pyrrolidin-3-yl methanesulfonate

Participants

Reaction Steps

A solution of 7.3 g of benzyl (R)-3-hydroxy-pyrrolidine-1-carboxylate and 5.56 ml of triethylamine in 80 ml of ethyl acetate was cooled to 0-5° C. under argon and treated within 30 minutes with a solution of 2.97 ml of mesyl chloride in 20 ml of ethyl acetate. After stirring at room temperature for 2 hours and leaving to stand for 16 hours the suspension was diluted with 40 ml of water, stirred for 10 minutes and the organic phase was separated. The organic phase was extracted in succession with 20 ml of 1N HCl, 20 ml of saturated NaHCO3 solution and 10 ml of saturated NaCl solution. The organic phase was dried over Na2SO4, filtered and the filtrate was concentrated to give 10.18 g of product as a beige oil.

Provenance & Evidence