693242-77-2Relevant academic research and scientific papers
Synthesis of buprenorphine from oripavine via N-demethylation of oripavine quaternary salts
Werner, Lukas,MacHara, Ales,Adams, David R.,Cox, D. Phillip,Hudlicky, Tomas
, p. 4628 - 4634 (2011)
Buprenorphine was synthesized from oripavine by a sequence involving the conversion of oripavine into its cyclopropylmethyl quaternary salt, N-demethylation with thiolate to N-cyclopropylmethyl nororipavine, and conversion of this material to the title compound by previously available methods. The new synthesis avoids toxic reagents used previously, is shorter, and proceeds in comparable yields. Experimental and spectral data are provided for all new compounds.
PROCESSES FOR THE PREPARATION OF MORPHINANE AND MORPHINONE COMPOUNDS
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Page/Page column 77-79, (2010/11/05)
The present application describes processes for the synthesis of morphinane and morphinone compounds, useful as pharmaceutical agents. Also included are novel intermediates useful in the preparation of these compounds. The process comprises quaternization of oripavine to provide a mixture of the R- and S-isomeric (at the nitrogen) quaternary salts. The R-isomer is readily isolated and converted to various N-(R)-morphinane and N-(S)-morphinone compounds. The R-isomer, S-isomer or a mixture of R- and S-isomers may be demethylated and converted to various morphinane and morphinone compounds.
