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Paper | Regular issue | Vol 38, No. 6, 1994, pp.1347-1354
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6691
Application of the Mitsunobu Reaction in the Morphine Series. Preparation of 6β-Amino-14β-hydroxymorphine and 14-Hydroxycodeine Derivatives

Csaba Simon, Sándor Hosztafi, and Sándor Makleit*

*Department of Research, Alkaloida Chemical Co. Ltd., H-4440 Tiszavasvári, POB 1, Hungary


By the application of the Mitsunobu reaction several 6β-phthalimido-14β-hydroxymorphine amd 14β-hydroxycodeine derivatives have been synthesized. Cleavage of the phthalimido derivatives with hydrazine hydrate afforded 6β-amino-14β-hydroxymorphine and 14β-hydroxycodeine derivatives. Catalytic hydrogenation of the Δ7,8 double bond offered a stereoselective way for the synthesis of the corresponding 6β-amino-14β-hydroxydihydrocoedine and 14β-hydroxydihydromorphine derivatives.