Partial Synthesis of 3-Deoxydihydromorphine from (—)-4-Hydroxy-6-keto-N-methylmorphinan
Year: 1979
Type: article
Abstract: Conversion of (-)-3-de~~dihydromorphine (3 into (-)-4-hydrony-6-keto-N-methylmorphinan (5) and reconversion of 2 into L via the ketone f : is described.The morphinan structure of 5 -was proven by reduction to the known (-)-4-hydroxy-Nmethylmorphinan (3.3-Deoxydihydromorphine (2) and 3-de~x~dih~dromorphinone (9, easily obtainable from dihydromorphine (9'.represent valuable intermediates for the preparation of a variety of anrinociceptive 3-deo~yopioids.~In addition the ketone 4, with the ether bridge linked at the u-position of the . ., carbonyl group, constitutes an important entry into the relatiyely unexplored class of 4-hydrolty-m~rphinans.~Such a conversion could be accomplished as fallows: 1. 8 1 = R 3 = OH, R 2 = H -
Source: Heterocycles
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W4239864342