title: Synthesis of buprenorphine from oripavine via N-demethylation of oripavine quaternary salts.
abstract: Buprenorphine was synthesized from oripavine by a sequence involving the conversion of oripavine into its cyclopropylmethyl quaternary salt, N-demethylation with thiolate to N-cyclopropylmethyl nororipavine, and conversion of this material to the title compound by previously available methods. The new synthesis avoids toxic reagents used previously, is shorter, and proceeds in comparable yields. Experimental and spectral data are provided for all new compounds.
authors.affiliation: Chemistry Department, Brock University, St. Catharines, Ontario, Canada.
authors.forename: Lukas
authors.initials: L
authors.lastname: Werner
authors.forename: Ales
authors.initials: A
authors.lastname: Machara
authors.forename: David R
authors.initials: DR
authors.lastname: Adams
authors.forename: D Phillip
authors.initials: DP
authors.lastname: Cox
authors.forename: Tomas
authors.initials: T
authors.lastname: Hudlicky
mesh_terms: D002047:Buprenorphine / Q000138:chemical synthesis*; D003488:Cyanogen Bromide / Q000737:chemistry; D055772:Green Chemistry Technology; D008745:Methylation; D009584:Nitrogen / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D013797:Thebaine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D012492:Salts; D013797:Thebaine; D002047:Buprenorphine; C005283:oripavine; D009584:Nitrogen; D003488:Cyanogen Bromide