Hydrochloric Acid → HCID 23324917, compound

Participants

Reaction Steps

A solution of 93.4 g of 3-(4-methylphenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester and β-(4-methylphenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester in 370 ml of 1 N aqueous sodium hydroxide solution is heated to 60° C. for four hours. Excess aqueous hydrochloric acid (1 N, 370 ml) is added and the solution concentrated under reduced pressure to give β-(4-methylphenyl)-5-oxo-2-pyrrolidinepropanoic acid and 3-(4-methylphenyl)-5-oxo-2-pyrrolidinepropanoic acid. The acids are dissolved in 300 ml of acetic anhydride, and the solution is heated to 90° C. The solution is filtered hot and the filtrate concentrated in vacuo. The oil is chromatographed on silica gel (200-400 mesh) (elution with chloroform) to give cis- and trans-dihydro-1-(4-methylphenyl)-1H-pyrrolizine-3,5(2H,6H)-diones as a white solid with mp 147°-150° C.

Provenance & Evidence