Methanesulfonyl chloride → Methanesulfonic acid 2-[benzyl-((S)-5-oxo-pyrrolidin-2-ylmethyl)-amino]-ethyl ester

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Reaction Steps

To a solution of (S)-(+)-5-((benzyl(2-hydroxyethyl)amino)methyl)pyrrolidin-2-one (3.5 g, 14.1 mmol) in ethanol-free CHCl3 (55 ml), TEA (2.85 g, 28.22 mmol) and methanesulfonyl chloride (3.23 g, 28.22 mmol, in 10 ml of CHCl3) were added at 0° C. The mixture was allowed to warm to room temperature and left stirring for 20 hours, then it was diluted with DCM (60 ml) and washed with a saturated solution of NaHCO3 (3×50 ml). After drying (Na2SO4) and removal of the solvent, the crude was purified by flash chromatography (DCM/abs EtOH/Petroleum Ether/33% NH4OH/Et2O 300/180/900/9.9/360 respectively) to afford the title compound (2.9 g, 63% yield).

Provenance & Evidence