1. Two-step iron(0)-mediated N-demethylation of N-methyl alkaloids.
- Author
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Kok GB, Pye CC, Singer RD, and Scammells PJ
- Subjects
- Methylation, Molecular Structure, Oxidation-Reduction, Alkaloids chemistry, Iron chemistry, Methylamines chemistry, Nitrogen Oxides chemistry
- Abstract
A mild and simple two-step Fe(0)-mediated N-demethylation of a number of tertiary N-methyl alkaloids is described. The tertiary N-methylamine is first oxidized to the corresponding N-oxide, which is isolated as the hydrochloride salt. Subsequent treatment of the N-oxide hydrochloride with iron powder readily provides the N-demethylated amine. Representative substrates include a number of opiate and tropane alkaloids. Key intermediates in the synthesis of semisynthetic 14-hydroxy pharmaceutical opiates such as oxycodone and oxymorphone are also readily N-demethylated using this method.
- Published
- 2010
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