Hydrochloric Acid → HCID 23324911, compound

Participants

Reaction Steps

A solution of 132.3 g of 3-(4-methoxyphenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester and β-(4-methoxyphenyl)-5-oxo-2-pyrrolidinepropanoic acid methyl ester in 480 ml of 1 N aqueous sodium hydroxide solution is heated to 60° C. for four hours. Excess aqueous hydrochloric acid (3 N, 170 ml) is added and the solution concentrated under reduced pressure to give β-(4-methoxyphenyl)-5-oxo-2-pyrrolidinepropanoic acid and 3-(4-methoxyphenyl)-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 dissolved in chloroform, treated with activated carbon, filtered and concentrated. The oil is chromatographed on silica gel (200-400 mesh) (elution with chloroform) to give cis-and trans-dihydro-1-(4-methoxyphenyl)-1H-pyrrolizine-3,5(2H,6H)-dione as a white solid with a mp 125°-127° C.

Provenance & Evidence