Direct and simple O-demethylation of thebaine to oripavine

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6774-

  Coop, Andrew ^a   Lewis, John W ^b   Rice, Kenner C ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OPIATE; ORIPAVINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 16044371531     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961473k     Document Type: Article

References (15)

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12. Oripavine was isolated as the oxalate salt from methanol. Thebaine was isolated as the (+)-tartaric acid salt from methanol.
13. Hauser, F. H.; Chen, T.-K.; Carroll, F. I. J. Med. Chem. 1974, 17, 1117.
14. It was found that oxidation of the dienol ether system with m-CPBA proceeded smoothly in water at room temperature in the presence of 1 equiv of sulfuric acid. Under these conditions thebaine gave 14-hydroxycodeinone in 87% yield.
15. Brown, J. J.; Hardy, R. A.; Roth, C. N. US Patent 3562279, 1971.