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New Methodology for the N-Demethylation of Opiate Alkaloids

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Zemin Dong and Peter J. Scammells*

Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, 381 Royal Parade, Parkville, Victoria 3052, Australia

J. Org. Chem., 2007, 72 (26), pp 9881–9885

DOI: 10.1021/jo071171q

Publication Date (Web): November 17, 2007

Section:

Alkaloids

Abstract

N-Demethylation is a key step in the preparation of a number of semisynthetic opiate pharmaceuticals. Herein we report a high-yielding, catalytic procedure for the N-demethylation of opiates which has a number of advantages over existing methods. For example, tetrasodium 5,10,15,20-tetra(4-sulfophenyl)porphyrinatoiron(II) (0.3 molar equiv) effected the transformation of codeine methyl ether to the corresponding N-nor analogue in 91% yield. The catalyst was readily removed and recycled.

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids
Gaik B. Kok, Cory C. Pye, Robert D. Singer and Peter J. Scammells
The Journal of Organic Chemistry2010 75 (14), 4806-4811
- Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids
  Gaik B. Kok, Cory C. Pye, Robert D. Singer and Peter J. Scammells
  The Journal of Organic Chemistry2010 75 (14), 4806-4811
  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 ...
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