Triethylamine → (5)-1-(4-Methylbenzyl)-2-oxopyrrolidin-3-yl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.51 ml, 3.6 mmol) was added to a cooled solution of (S)-3-hydroxy-1-(4-methylbenzyl)pyrrolidin-2-one (0.5 g, 2.4 mmol) in anhydrous DCM (12.2 ml) at 0° C. under a nitrogen atmosphere. Methanesulfonyl chloride (0.2 ml, 2.6 mmol) was then added dropwise and the reaction was allowed to stir at 0° C. for 15 min before quenching with a satd. sodium bicarbonate solution (10 mL). The mixture was allowed to warm to rt and the aqueous layer was separated and extracted with DCM (2×). The combined oranic layers were dried over MgSO4 and evaporated in vacuo to give a white solid (0.73 g) which was then purified by silica gel chromatography (40 g of silica) eluting with a gradient of 0% to 50% ethyl acetate in hexanes to provide 0.63 g (91%) of the desired product as a white solid.

Provenance & Evidence