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Related Experiment Videos

Efficient synthesis of 14-hydroxymorphinans from codeine

M A Schwartz, R A Wallace

    Journal of Medicinal Chemistry
    |December 1, 1981
    PubMed
    Summary

    This study details a synthetic route for noroxycodone and noroxymorphone from codeine. Key steps involve N-demethylation, oxidation, and singlet oxygen reactions for efficient opioid analog production.

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    Area of Science:

    • Organic Chemistry
    • Medicinal Chemistry
    • Synthetic Chemistry

    Background:

    • Codeine is a widely used opioid analgesic.
    • Developing efficient synthetic routes to related opioid analogs is crucial for research and potential therapeutic applications.
    • Noroxycodone and noroxymorphone are important opioid derivatives.

    Purpose of the Study:

    • To establish a multi-step synthetic pathway for noroxycodone and noroxymorphone starting from codeine.
    • To optimize key chemical transformations, including N-demethylation, oxidation, and singlet oxygen reactions.
    • To report overall yields for the synthesis of these opioid compounds.

    Main Methods:

    • N-Demethylation and oxidation of codeine to N-(ethoxycarbonyl)norcodeinone.
    • Conversion to a dienol acetate derivative followed by singlet oxygen oxidation to N-(ethoxycarbonyl)-14-hydroxynorcodeinone.
    • Hydrogenation and acid hydrolysis for noroxycodone synthesis; O-demethylation for noroxymorphone synthesis.

    Main Results:

    • Noroxycodone synthesized in six steps with a 52% overall yield.
    • Noroxymorphone synthesized in seven steps with a 43% overall yield.
    • The key singlet oxygen oxidation step was optimized.

    Conclusions:

    • An effective synthetic route from codeine to noroxycodone and noroxymorphone has been developed.
    • The described methodology provides access to important opioid analogs.
    • The study highlights the utility of singlet oxygen in synthesizing complex opioid structures.

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