N-Demethylation of N-methyl alkaloids with ferrocene

被引：24

作者：

Kok, Gaik B. ^{[1
]}

Scammells, Peter J. ^{[1
]}

机构：

[1] Monash Univ, Med Chem & Drug Act, Monash Inst Pharmaceut Sci, Parkville, Vic 3052, Australia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 15期

关键词：

N-Demethylation; Polonovski reaction; Alkaloid; Ferrocene; NONCLASSICAL POLONOVSKI REACTION; OPIATE ALKALOIDS; MORPHINE ALKALOIDS; MUCOR PIRIFORMIS; THEBAINE; CODEINE;

D O I：

10.1016/j.bmcl.2010.06.031

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Under Polonovski-type conditions, ferrocene has been found to be a convenient and efficient catalyst for the N-demethylation of a number of N-methyl alkaloids such as opiates and tropanes. By judicious choice of solvent, good yields have been obtained for dextromethorphan, codeine methyl ether, and thebaine. The current methodology is also successful for the N-demethylation of morphine, oripavine, and tropane alkaloids, producing the corresponding N-nor compounds in reasonable yields. Key pharmaceutical intermediates such oxycodone and oxymorphone are also readily N-demethylated using this approach. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4499 / 4502

页数：4

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