Hydrochloric Acid → 5-Oxo-2-pyrrolidinepropanoic acid p-chlorobenzyl ester

Participants

Reaction Conditions

Reaction Steps

Five grams of dihydro-1H-pyrrolizine-3,5(2H,6H)-dione (III) are dissolved in 31 g of p-chlorobenzyl alcohol and 0.2 ml of concentrated hydrochloric acid is added. The solution is heated at 100° C. for 65 hours. The mixture is cooled and chromatographed over silica gel in dichloromethane. The starting p-chlorobenzyl alcohol is eluted with dichloromethane and the product is eluted with 2.5% methanol in dichloromethane. The eluate containing the product is concentrated at reduce pressure and the residual oil solidifies upon standing. The solid is recrystallized from toluene diethyl ether to yield 5-oxo-2-pyrrolidinepropanoic acid p-chlorobenzyl ester with a melting point of 63°-64° C.

Provenance & Evidence