Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.