| Conversion of Thebaine to Codeine. | |
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MedLine Citation:
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PMID: 994146 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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An improved conversion of thebaine to codeine has been developed. Oxymercuration of thebaine with mercuric acetate in refluxing methanol, followed by hydrolysis of the intermediate 7-acetomercurineopinone dimethyl ketal with 3 N acetic acid, or, alternatively, reduction of the organomercury compound with sodium borohydride and mild acid hydrolysis of the resulting neopinone dimethyl ketal, gives neopinone in 95-100% yields. Either acid- or alkali-catalyzed isomerization to codeinone leads to the equilibrium mixture consisting of codeinone-neopinone, 3:1. Complete conversion to codeinone in 85-90% yield results from treatment of neopinone with anhydrous hydrogen chloride or hydrogen bromide in ether-methylene chloride, followed by elimination of hydrogen halide from the intermediate 8-halodihydrocodeinone. The known borohydride reduction of codeinone then gives codeine in 85% overall yield from thebaine. |
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Authors:
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R B Barber; H Rapoport |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 19 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 1976 Oct |
Date Detail:
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Created Date: 1977-01-29 Completed Date: 1977-01-29 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 1175-80 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Codeine
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chemical synthesis* Dealkylation Magnetic Resonance Spectroscopy Molecular Conformation Oxidation-Reduction Thebaine* |
| Chemical | |
Reg. No./Substance:
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115-37-7/Thebaine; 76-57-3/Codeine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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