Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-5-(benzyloxy)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

At ambient temperature and under an inert atmosphere, 4.40 g of 5-benzyloxypyrrolidin-2-one is added to a solution of 4.64 g of sodium bis(trimethylsilyl) amide in 350 cm3 of anhydrous ethyl ether. The mixture is agitated for 30 minutes, then cooled to 0° C., and a solution of 4.06 g of benzenesulphonyl chloride in 30 cm3 of anhydrous ether is added, while maintaining the temperature at 0° C. The temperature is allowed to return to the ambient, then, after filtering and evaporating the solvent under reduced pressure, the residue is chromatographed on silica, eluting with a mixture of ethyl acetate and n-hexane (1-2). After re-crystallizing from a mixture of benzene and n-hexane (1-3), 2.25 g of the expected product is obtained, m.p. 80°-81° C.

Provenance & Evidence