Journal of Organic Chemistry 2011-06-03

Synthesis of buprenorphine from oripavine via N-demethylation of oripavine quaternary salts.

Lukas Werner, Ales Machara, David R Adams, D Phillip Cox, Tomas Hudlicky

Index: J. Org. Chem. 76(11) , 4628-34, (2011)

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Abstract

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.