Efficient N-demethylation of opiate alkaloids using a modified nonclassical Polonovski reaction.
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.
McCamley
Kristy
K
Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville, Victoria 3052, Australia.
Ripper
Justin A
JA
Singer
Robert D
RD
Scammells
Peter J
PJ
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
D000470:Alkaloids; D000588:Amines; D000701:Analgesics, Opioid; D005290:Ferric Compounds; D009294:Narcotics; D010087:Oxides; C024823:ferric sulfate