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  • Oxycodone Synthesis

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    PoloGreen
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    The document summarizes the synthesis of oxycodone from thebaine. It involves two steps - first thebaine is treated with hydrogen peroxide and formic acid to produce 14-hydroxycodeinone. This intermediate is then hydrogenated using palladium on carbon to yield oxycodone hydrochloride. An alternative synthesis of the key intermediate 14-hydroxycodeinone is also presented, which uses m-chloroperoxybenzoic acid to oxidize thebaine.

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    The document summarizes the synthesis of oxycodone from thebaine. It involves two steps - first thebaine is treated with hydrogen peroxide and formic acid to produce 14-hydroxycodeinone. This intermediate is then hydrogenated using palladium on carbon to yield oxycodone hydrochloride. An alternative synthesis of the key intermediate 14-hydroxycodeinone is also presented, which uses m-chloroperoxybenzoic acid to oxidize thebaine.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
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    1K views3 pages

    Oxycodone Synthesis

    Uploaded by

    PoloGreen
    The document summarizes the synthesis of oxycodone from thebaine. It involves two steps - first thebaine is treated with hydrogen peroxide and formic acid to produce 14-hydroxycodeinone. This intermediate is then hydrogenated using palladium on carbon to yield oxycodone hydrochloride. An alternative synthesis of the key intermediate 14-hydroxycodeinone is also presented, which uses m-chloroperoxybenzoic acid to oxidize thebaine.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
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    of 3

    Oxycodone

    CH3O

    O HO O H N

    14-hydroxydihydrocodeinone Oxycodone HCl Oxynorm - Nppp o Tablets Oxycontin - Napp o Tablets

    Oxycodone terephthalate Endodan - (US only) Tablets


    CH3O COO

    O HO O H N+ H COO

    oxycodone terephthalate

    Oxycodone synthesis
    hydrogen peroxide
    O H O O O H N O OH OCH3 OH

    H O CH3O N O H CH3O N

    O H

    OCH3

    HCOOH, H2O2, H2O iPrOH, 0-5oC, 2h, o then 45 C, 3h 1,4-addition H+


    CH3O

    thebaine

    OCH3

    OCH3

    WO Patent 2004108090
    CH3O CH3O

    O HO O H N

    H2, 5% Pd/C 30-40 psi, rt, 20h

    O HO O H N

    MeOH

    O H N

    HO hemiketal hydrolysis CH3O OH

    oxycodone o m.p. 218-220 C EtOH conc HCl in iPrOH

    14-hydroxycodeinone 90% yield

    oxycodone HCl m.p. 270-272oC (dec.)

    Alternative synthesis of 14-hydroxycodeinone intermediate

    O O CH3O Cl N O H CH3O N O OCH3 O H Cl

    mCPBA mCPBA AcOH/CF3COOH heat 1,4-addition


    CH3O N

    OH OCH3

    thebaine aq. H
    Cl
    +

    OCH3 OH N O OH OH OCH3

    OCH3

    O HO CH3O OH H N

    OCH3

    CH3O

    aq. H+

    J. Med. Chem., 1974, 17, 1117


    O HO O H N

    MeOH hemiketal hydrolysis

    14-hydroxycodeinone

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