title: Efficient N-demethylation of opiate alkaloids using a modified nonclassical Polonovski reaction.
abstract: A modified Polonovski reaction has been employed to N-demethylate several opiate alkaloids in moderate to high yield. This method provides an alternative to traditional N-demethylation procedures which utilize toxic reagents such as cyanogen bromide or expensive reagents such as vinyl chloroformate. The current synthesis involves N-oxide formation, isolation of the corresponding N-oxide hydrochloride, and an FeSO(4).7H(2)O mediated Polonovski reaction to afford the desired secondary amine.
authors.affiliation: Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville, Victoria 3052, Australia.
authors.forename: Kristy
authors.initials: K
authors.lastname: McCamley
authors.forename: Justin A
authors.initials: JA
authors.lastname: Ripper
authors.forename: Robert D
authors.initials: RD
authors.lastname: Singer
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Scammells
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D000701:Analgesics, Opioid / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry; D007536:Isomerism; D008745:Methylation; D009294:Narcotics / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry
chemical_list: D000470:Alkaloids; D000588:Amines; D000701:Analgesics, Opioid; D005290:Ferric Compounds; D009294:Narcotics; D010087:Oxides; C024823:ferric sulfate