Further investigation of the N-demethylation of tertiary amine alkaloids using the non-classical Polonovski reaction.
The iron salt-mediated Polonovski reaction efficiently N-demethylates certain opiate alkaloids. In this process, the use of the hydrochloride salt of the tertiary N-methyl amine oxide was reported to give better yields of the desired N-demethylated product. Herein, we report further investigation into the use of N-oxide salts in the iron salt-mediated Polonovski reaction. An efficient approach for the removal of iron salts that greatly facilitates isolation and purification of the N-nor product is also described.
Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville, Vic. 3052, Australia.
Shanti
S
Thavaneswaran
Peter J
PJ
Scammells
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D003061:Codeine / Q000737:chemistry; D007501:Iron / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry
D000470:Alkaloids; D000588:Amines; D010087:Oxides; D007501:Iron; D003061:Codeine