A novel synthesis of [O-methyl-14C]dextromethorphan: utility of the vinyloxycarbonyl group

A novel, selective approach to [O‐methyl‐14C]Dextromethorphan is presented. The key feature is protection of 3‐hydroxymorphinan at nitrogen and oxygen with the vinyloxycarbonyl group. This allows selective O‐deprotection and methylation without competing nitrogen quaternization. The N‐vinyloxy carbo...

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Bibliographic Details
Published in:	Journal of labelled compounds & radiopharmaceuticals Vol. 43; no. 13; pp. 1283 - 1288
Main Authors:	Senderoff, S.G., Landvatter, S.W., Heys, J.R.
Format:	Journal Article
Language:	English
Published:	Chichester, UK John Wiley & Sons, Ltd 01-11-2000 Wiley
Subjects:	Biological and medical sciences Carbon-14 Contrast media. Radiopharmaceuticals Dextromethorphan Medical sciences morphinan Pharmacology. Drug treatments vinyl chloroformate vinyloxycarbonyl protecting group Morphinan derivatives Protecting group Radiolabelling Nitrogen heterocycle Opiates Antitussive agent Dextromethorphan Vinylic compound Aromatic compound Hydrobromides Iodomethane Methylation Chemical synthesis Carbon 14
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Summary:	A novel, selective approach to [O‐methyl‐14C]Dextromethorphan is presented. The key feature is protection of 3‐hydroxymorphinan at nitrogen and oxygen with the vinyloxycarbonyl group. This allows selective O‐deprotection and methylation without competing nitrogen quaternization. The N‐vinyloxy carbonyl group is converted to the desired methyl group by lithium aluminum hydride reduction. Copyright © 2000 John Wiley & Sons, Ltd.
Bibliography:	ArticleID:JLCR417 istex:8C13DFF2AE0B27C82BB420083DBE96609A16D55A ark:/67375/WNG-CTVLT99R-P
ISSN:	0362-4803 1099-1344
DOI:	10.1002/1099-1344(200011)43:13<1283::AID-JLCR417>3.0.CO;2-C