title: Further investigations into the N-demethylation of oripavine using iron and stainless steel.
abstract: Further investigations into the direct synthesis of N-nororipavine from oripavine using iron powder under non-classical Polonovski conditions have been conducted. The stoichiometry, solvents and iron oxidation rates were found to have a dramatic effect on the rate of N-demethylation as well as product yield. Herein, we also present high-yield access to the N-demethylated product simply by employing stainless steel rather than iron powder as redox catalyst. To our knowledge, this is the first time stainless steel has been used to moderate the redox chemistry of iron in organic synthesis.
authors.affiliation: Medicinal Chemistry and Drug Action, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, Victoria, 3052, Australia.
authors.forename: Gaik B
authors.initials: GB
authors.lastname: Kok
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Scammells
mesh_terms: D002384:Catalysis; D007501:Iron / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013193:Stainless Steel / Q000737:chemistry*; D013797:Thebaine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D013193:Stainless Steel; D013797:Thebaine; C005283:oripavine; D007501:Iron