Process for the preparation of oripavine derivative

Details Process for the preparation of oripavine derivative Process for the preparation of oripavine derivative

C - Chemistry, Metallurgy

07

D

260/237.65

C07D 489/12 (2006.01)

Patent

CA 1212108

ABSTRACT OF THE DISCLOSURE A process for the preparation of the compound N-cyclopropylmethyl-6,14-endoethano-7-(2-hydroxy-2- methyl-2-ter-butyl)-tetrahydronororipavine which comprises reacting thebaine with acrolein to undergo Diels-Alder reaction to give 6,14-endoethano-7-formyl-tetrahydrothe- baine. This is reacted with methyl magnesium iodide to give 6,14-endoethano-7-(2-hydroxy-2-methyl)-tetrahydrothebaine which is oxidized by reaction with potassium permanganate to give 6,14-endoethano-7-acetyl-tetrahydrothebaine which is hydrogenated using palladium catalyst to give 6,14-endoethano-7-acetyltetrahydrothebaine. Reaction with ter-butyl magnesium chloride gives 6,14-endoethano- 7-(2-hydroxy-2-methyl-2-ter-butyl)-tetxahydrothebaine which is reacted with cyanogen bromide to give N-cyano-6,14- endoethano-7-(2-hydroxy-2-methyl-2-ter-butyl) tetrahydro- thebaine which is reacted with cyanoyen bromide to give N-cyano-6,14-endoethano-7-(2-hydroxy-2-methyl-2-terbutyl)- tetrahydrothebaine which is demethylated by treatment with potassium hydroxide in one pot at 210°C to give 6,14-endoethano-7-(2-hydroxy-2-methyl-2-ter-butyl)-tetra- hydronororipavine which on treatment with cyclo-propyl methyl bromide gives the compound N-cyclo-propylmethyl- 6,14-endoethano-7-(2-hydroxy-2-methyl-2-ter-butyl)-tetra- hydronororipavine. The process proceeds smoothly with readily available reactants, and yields a pure product, advantages over the prior art.

442036

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