O-Demethylation of opioid derivatives with methane sulfonic acid/methionine: Application to the synthesis of naloxone and analogues

Article abstract of DOI:10.1080/00397919208019086

Naloxone 2 was obtained by demethylation of N-allylnoroxycodone 1 with methane sulfonic acid/methionine. This reagent is an excellent substitute for boron tribromide. It was used for the synthesis of analogous derivatives with variable results.

Full text of DOI:10.1080/00397919208019086

This article was downloaded by: [Duke University Libraries]
On: 10 June 2012, At: 06:25
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH,
UK
Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
Publication details, including instructions for
authors and subscription information:
http://www.tandfonline.com/loi/lsyc20
O-Demethylation of Opioid
Derivatives with Methane
Sulfonic Acid/ Methionine:
Application to the Synthesis of
Naloxone and Analogues
Jean-Daniel Andre a , Jean-Robert Dormoy a & Alain
Heymes a
a Sanofi-Chimie, Route de Gap, BP 15, 04201,
Sisteron, Cedex, France
Available online: 23 Sep 2006
To cite this article: Jean-Daniel Andre, Jean-Robert Dormoy & Alain Heymes (1992):
O-Demethylation of Opioid Derivatives with Methane Sulfonic Acid/ Methionine:
Application to the Synthesis of Naloxone and Analogues, Synthetic Communications:
An International Journal for Rapid Communication of Synthetic Organic Chemistry,
22:16, 2313-2327
To link to this article: http://dx.doi.org/10.1080/00397919208019086
PLEASE SCROLL DOWN FOR ARTICLE
Full terms and conditions of use: http://www.tandfonline.com/page/terms-
and-conditions

This article may be used for research, teaching, and private study purposes.
Any substantial or systematic reproduction, redistribution, reselling, loan,
sub-licensing, systematic supply, or distribution in any form to anyone is
expressly forbidden.
The publisher does not give any warranty express or implied or make any
representation that the contents will be complete or accurate or up to
date. The accuracy of any instructions, formulae, and drug doses should be
independently verified with primary sources. The publisher shall not be liable
for any loss, actions, claims, proceedings, demand, or costs or damages
whatsoever or howsoever caused arising directly or indirectly in connection
with or arising out of the use of this material.