4-Toluenesulfonyl chloride → (R)-(1-methyl-5-oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate

Participants

Reaction Steps

Triethylamine (5.26 mL), trimethylamine hydrochloride (1.07 g) and 4-methylbenzenesulfonyl chloride (5.6 g) were sequentially added to a solution of (R)-5-(hydroxymethyl)-1-methylpyrrolidin-2-one (2.93 g, 48.3 g, described in J. Med. Chem., 34(3), 1991, 887-900) in chloroform (40 mL) under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure to give (R)-(1-methyl-5-oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate as a yellow amorphous (6.6 g).

Provenance & Evidence