Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Note | Regular issue | Vol 68, No. 4, 2006, pp.837-840
Published online, 10th March, 2006
DOI: 10.3987/COM-06-10694
Methylation of Non-acidic Alcohols of Alkaloids with TMS-diazomethane: Conversion of Codeine to Codeine-6-methyl Ether

Christopher W. Cunningham, Linn N. Thatcher, and Andrew Coop*

*Department of Pharmceutcial Sciences, School of Pharmacy, University of Maryland, 20 Penn Street, Baltimore, MD 21201, U.S.A.

Abstract

Trimethylsilyldiazomethane (TMS-CHN2) is a convenient agent for the methylation of acidic alcohols, and is known to methylate non-acidic alcohols in CH2Cl2 by the addition of HBF4. Herein, we show that silica gel acts as a suitable alternative for alkaloids, without causing precipitation of the salt from the reaction mixture.