Convenient synthesis of (S)-(+)-apomorphine from (R)-(-)-apomorphine.
A method was devised for preparing (S)-(+)-apomorphine from (R)-(-)-apomorphine. Dehydrogenation of the dimethyl ether of (R)-(-)-apomorphine with 10% palladium-on-carbon followed by reduction with sodium cyanoborohydride under acidic conditions resulted in quantitative racemization to give (R,S)-apomorphine dimethyl ether, which then was resolved with (-)-tartaric acid. Ether cleavage of (S)-(+)-apomorphine dimethyl ether (-)-tartrate with hydriodic acid in acetic anhydride yielded (S)-(+)-apomorphine, which was isolated as the hydrochloride salt in 99% enantiomeric excess.
D001058:Apomorphine / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D008722:Methods; D013237:Stereoisomerism
D001058:Apomorphine