Issue 4, 2011

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.

Graphical abstract: Further investigations into the N-demethylation of oripavine using iron and stainless steel

Supplementary files

Article information

Article type
Communication
Submitted
12 Nov 2010
Accepted
03 Dec 2010
First published
24 Dec 2010

Org. Biomol. Chem., 2011,9, 1008-1011

Further investigations into the N-demethylation of oripavine using iron and stainless steel

G. B. Kok and P. J. Scammells, Org. Biomol. Chem., 2011, 9, 1008 DOI: 10.1039/C0OB01021A

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