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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.