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    Cocaine For Tropinone

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    Cocaine For Tropinone

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    tropinone

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    Cocaine for Tropinone

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    Cocaine For Tropinone

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    Tropane Alkaloids || A Review

    Synthesis of ecgonine & its derivatives

    Contents
    1. 1 Ecgonine
    1. 1.1 2-Carbomethoxytropinone
    2. 1.2 Cocaine
    3. 1.3 Cocaethylene
    Ecgonine
    1. Ecgonine can be prepared from 2-carbomethoxytropinone, first by
    reducing it, then hydrolysis.

    2. Tropinone can be used as a starting material for ecgonine


    synthesis.
    R. Willsttter and W. Mller, Ber. Dtsch. Chem. Ges., 1898, 31, 2655
    2-Carbomethoxytropinone

    01. Cyclization of 1-methyl-2,5-dicarboethoxypyrrolidine gives 2-


    Carbomethoxytropinone.
    R. Willstatter and M. Bommer, Ann., 422, 15 (1921)
    R. Willstiitter and A. Pfannenstiehl, Ann., 422, 1 (1921)

    02. 2-Carbomethoxytropinone can be obtained from modified


    Robinson synthesis. (yield 20%).
    German Patent 345,759

    03. 2-Carbomethoxytropinone can be produced from Tropinone and


    carbon dioxide in presence of sodium (or potassium) in benzene (or
    xylene). Practically dimethyl carbonate is used as a source of carbon
    dioxide. (yield 70-80%).
    N. A. Preobrashenski, M. N. Schtschukina, and R. A. Lapina, Ber., 69,1615 (1936)
    04. Willstatter's synthesis proceeds using dipotassium salt of
    monomethyl beta-ketoglutarate.
    R. Willstatter, 0. Wolfes, and H. Miider, Ann., 434, 111 (1923)

    05. 2-Carbomethoxytropinone is obtained at a high yield from


    modified Robinson synthesis.

    06. Variation of Willstatter's synthesis using monomethyl beta-


    ketoglutarate also yields 2-carbomethoxytropinone in satisfactory
    quantity.
    R. Willstiitter and A. Pfannenstiehl, Ann., 422, 1 (1921)
    R. Kaushall, J. Indian Chem. SOL, 17,138 (1940)
    Cocaine

    01. Willstters Preparation

    Cocaine was first prepared in 1923 by Willstter. This synthesis


    is very remarkable because, although at this time both the
    relative and the absolute stereochemistry of cocaine were
    unknown, they were able to prepare this alkaloid in optically
    active form.
    WILLSTTTER, R.; WOLFES, O.; MDER, H. Annalen 1923, 434, 111

    02. Preobrazhenskiis Preparation

    In 1958 a group of Soviet chemists made improvements


    to Willstter's synthesis by the in situ generation of the unstable
    butandial by acidic hydrolysis of dimethoxytetrahydrofuran.

    BAZILEVSKAYA, G.I.; BAINOVA, M.S.; GURA, D.V.; DYUMAEV, K.M.; PREOBRAZHENSKII, N.A.
    Isvest.Vysshikh.Ucheb.Zavedenii, Khim. i Khim.Tekhnol. 1958, 2, 75-81 (Chem.Abstr. 1959, 53, 423h).

    BAINOVA, M.S.; BAZILEVSKAYA, G.I.; DYUMAEV, K.M.; PREOBRAZHENSKII,


    N.A. Zh.Obshch.Khim. 1960, 30, 1120-1123 (Chem.Abstr.1961, 55, 530f)

    BAINOVA, M.S.; BAZILEVSKAYA, G.I.; PREOBRAZHENSKII, N.A.


    Zh.Obshch.Khim. 1960, 30, 3258-3261 (Chem.Abstr. 1961, 55, 21155d)

    02. Tufariello synthesis using nitrone


    TUFARIELLO, J.J.; TEGELER, J.J.; WONG, S.C.; ALI, S.A. Tetrahedron Lett. 1978, 30, 1733-1736

    TUFARIELLO, J.J.; MULLEN, G.B.; TEGELER, J.J.; TRYBULSKI, E.J.; WONG, S.C.; ALI, S.A.
    J.Am.Chem.Soc. 1979, 101, 2435-2442

    04. Carrolls Preparation


    LEWIN, A.H.; NASEREE, T.; CAROLL, F.I. J.Heterocycl.Chem. 1987, 24, 19-21

    CARROLL, F.I.; COLEMAN, M.L.; LEWIN, A.H. J.Org.Chem. 1982, 47, 13-19

    05. Rapoports Preparation

    LIN, R.; CASTELLS, J.; RAPOPORT, H. J.Org.Chem. 1998, 63, 4069-4078

    PETERSEN, J.S.; FELS, G.; RAPOPORT, H. J.Am.Chem.Soc. 1984, 106, 4539-4547

    06. Chas Preparation


    LEE, J.C.; LEE, K.; CHA, J.K. J.Org.Chem. 2000, 65, 4773-4775

    03. Pearson synthesis

    Cocaethylene

    01. Cocaethylene can be prepared from cocaine and ethanol by an


    ester exchange reaction.

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    Update: This web page was last updated on January 04 2014 at 00:00.

    License: Tropane Alkaloids by Lab-Q is licensed under a Creative Commons Attribution-Non


    Commercial-Share Alike 4.0 International License.
    Disclaimer: For information purposes only. Information accuracy not guaranteed. No
    professional advice given. Also no liability implied or taken.

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