METHOD OF PREPARING 17-CYCLOPROPYLMETHYL-6-4-ENDO-ETHANO-7-(2-HYDROXY- 3,3-DIMETHYLBUT-2-YL)TETRAHYDRO-17-NORORIPAVINE Russian patent published in 1999 - IPC

FIELD: organic synthesis. SUBSTANCE: synthesis of title compound includes Diels- Alder interaction of thebaine with methyl vinyl ketone followed by hydrogenation of double bond of resultant 6,14-endo-etheno-7alpha- acetyltetrahydrothebaine in reactor column with fixed palladium-on- carbon catalyst bed at pressure 3-3.5 Mpa and elevated temperature and subsequent Grignard alkylation of 6,14-endo-ethano-7alpha- acetyltetrahydrothebaine obtained with tert-butylmagnesium chloride in presence of equimolar amount of tert-butyl alcohol or anhydrous magnesium chloride to give 6,14-endo-ethano-7-(2-hydroxy-3,3- dimethylbut-2-yl)tetrahydrothebaine. The latter is subjected to Brown N- demethylation reaction involving bromocyan prepared in situ from sodium cyanide and bromine and resultant N-cyano derivative is brought into reaction with cyclopropylcarbonyl chloride in presence of anhydrous potassium carbonate. Non-isolated product is finely reduced with lithium aluminum hydride in tetrahydrofuran. EFFECT: simplified synthesis due to reduced number of operations and increased safety due to using less explosive and less toxic reagents. 1 dwg, 6 ex