(5S)-5-(2-Methylpropyl)pyrrolidine-2,4-dione → HCID 11768826, compound

Participants

Reaction Steps

A solution of 5 g of (S)-5-(2-methylpropyl)-2,4-pyrrolidinedione in 250 ml of ethanol is treated with 2 g of Raney nickel (washed to neutral) and exposed to hydrogen gas at 50 pounds per square inch (psi). After 5 hours, hydrogen uptake ceases, the catalyst is filtered and the filtrate evaporated to a gum. The gum is taken up in chloroform and the chloroform is evaporated. The resulting gum is dissolved in chloroform, filtered through a 250 ml bed of silica gel in chloroform and eluted with chloroform-methanol (96:4) to afford 3.2 g of (4S-cis)-4-hydroxy-5-(2-methylpropyl)-2-pyrrolidinone after crystallization from 12 ml of hot ethyl acetate, 120 ml isopropyl ether and gradual cooling to 10° C.; mp 71°-73° C. [α]D23 =-19° (C=0.7% chloroform).

Provenance & Evidence