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115-37-7Relevant articles and documents
Alternative methods for the MnO2 oxidation of codeine methyl ether to thebaine utilizing ionic liquids
Singer, Robert D,Scammells, Peter J
, p. 6831 - 6833 (2001)
The MnO2 oxidation of codeine methyl ether, CME, to thebaine has been accomplished via the use of the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate, bmimBF4. The ionic liquid has been used to remove or extract excess MnO
A novel synthesis of thebaine from codeine
Coop, Andrew,Rice, Kenner C.
, p. 43 - 47 (1998)
Codeine was converted into thebaine through methylation of the enolate of codeinone.
Rearrangement of 5-trimethylsilylthebaine on treatment with L-selectride: An efficient synthesis of (+)-bractazonine
Chen, Weibin,Wu, Huifang,Bernard, Denzil,Metcalf, Matthew D.,Deschamps, Jeffrey R.,Flippen-Anderson, Judith L.,MacKerell Jr., Alexander D.,Coop, Andrew
, p. 1929 - 1932 (2003)
Treatment of 5-trimethylsilylthebaine with L-Selectride gave rise to a rearrangement to 10trimethylsilylbractazonine through migration of the phenyl group, whereas treatment of thebaine with strong Lewis acids is known to lead to a similar rearrangement through migration of the alkyl bridge to give, after reduction, (+)-neodihydrothebaine. It is suggested that the rearrangement of the alkyl group of thebaine is favored due to the formation of a tertiary benzylic cation. However, for 5-trimethylsilylthebaine, the lithium ion of L-Selectride acts as the Lewis acid and the β-silyl effect dominates in the stabilization of any positive charge. This rearrangement provides a clear example of the greater relative migratory aptitude of phenyl groups over alkyl groups, and provides an efficient synthesis of (+)-bractazonine from thebaine.
Relationship of pharmacokinetic and metabolic parameters to the absence of physical dependence liability with thebaine 3H
Misra,Pontani,Mule
, p. 1108 - 1110 (1973)
The rapid metabolism, excretion and elimination of thebaine from rat brain produces no biochemical changes in the cells of the central nervous system, which could be the reason for its low physiological tolerance.
Two-step iron(0)-mediated N-demethylation of N -methyl alkaloids
Kok, Gaik B.,Pye, Cory C.,Singer, Robert D.,Scammells, Peter J.
, p. 4806 - 4811 (2010)
(Figure Presented) A mild and simple two-step Fe(0)-mediated N-demethylation of a number of tertiary N-methyl alkaloids is described. The tertiary N-methylamine is first oxidized to the corresponding N-oxide, which is isolated as the hydrochloride salt. Subsequent treatment of the N-oxide hydrochloride with iron powder readily provides the N-demethylated amine. Representative substrates include a number of opiate and tropane alkaloids. Key intermediates in the synthesis of semisynthetic 14-hydroxy pharmaceutical opiates such as oxycodone and oxymorphone are also readily N-demethylated using this method.
ESR ANALYSIS OF THE KINETIC ALKALINITY OF PSEUDOEPHEDRINE
Masalimov, A. S.,Nikol'skii, S. N.,Abdykarimova, A. P.,Prokof'ev, A. I.,Muldakhmetov, Z. M.
, p. 1559 - 1562 (1992)
The kinetics of protonation of pseudoephedrine by 3,6-di-tert-butyl-2-hydroxyphenoxyl have been analyzed by the ESR technique.It was shown that protolysis of the radical produced closed ionic pairs with the pseudoephedrine cation in a dimer state. Keywords: ESR, pseudoephedrine, 3,6-di-tert-butyl-2-hydroxyphenoxyl, ion pairs.
Manganese dioxide allylic and benzylic oxidation reactions in ionic liquids
Hemeon, Ivan,Barnett, Neil W.,Gathergood, Nicholas,Scammells, Peter J.,Singer, Robert D.
, p. 125 - 128 (2004)
Ionic liquids 1-butyl-3-methylimidazolium tetrafluoroborate [bmIm][BF4] and 1-butyl-3-methylimidazolium hexafluorophosphate [bmIm][PF6] were evaluated as reaction media for allylic and benzylic oxidation reactions using manganese dioxide. The use of ionic liquids as an extractant in the reaction work-up was also investigated. Procedures for recycling of the [bmIm][PF6] ionic liquids used in these MnO2 oxidation reactions were also developed.
Closure of the oxide bridge in morphine biosynthesis
Lenz, Rainer,Zenk, Meinhart H.
, p. 3897 - 3900 (1994)
A highly substrate specific enzyme has been discovered and purified to homogeneity, which transfers the acetyl-moiety from acetyl-coenzyme A to the 7-OH group of salutaridinol. The formed 7-O-acetyl-salutaridinol spontaneously closes the oxide bridge at pH 8-9 by allylic elimination furnishing the morphine precursor thebaine.
A Regio- and Diastereoselective Anodic Aryl–Aryl Coupling in the Biomimetic Total Synthesis of (?)-Thebaine
Lipp, Alexander,Ferenc, Dorota,Gütz, Christoph,Geffe, Mario,Vierengel, Nina,Schollmeyer, Dieter,Sch?fer, Hans J.,Waldvogel, Siegfried R.,Opatz, Till
supporting information, p. 11055 - 11059 (2018/08/21)
The biosynthesis of thebaine is based on the regioselective, intramolecular, oxidative coupling of (R)-reticuline. For decades, chemists have sought to mimic this coupling by using stoichiometric oxidants. However, all approaches to date have suffered from low yields or the formation of undesired regioisomers. Electrochemistry would represent a sustainable alternative in this respect but all attempts to accomplish an electrochemical synthesis of thebaine have failed so far. Herein, a regio- and diastereoselective anodic coupling of 3′,4′,5′-trioxygenated laudanosine derivatives is presented, which finally enables electrochemical access to (?)-thebaine.
Polonovski-type N-demethylation of N-methyl alkaloids using substituted ferrocene redox catalysts
Kok, Gaik B.,Scammells, Peter J.
experimental part, p. 2587 - 2594 (2012/09/22)
Various substituted ferrocenes have been trialed as catalysts in the nonclassical Polonovski reaction for N-demethylation of N-methyl alkaloids. Earlier studies suggest that conditions facilitating a higher ferrocenium ion concentration lead to superior outcomes. In this regard, the bifunctional ferrocene FcCH2CO2H, with electron donor and acceptor moieties in the same molecule, has been shown to be advantageous for use as a catalyst in the N-demethylation of a number of tertiary N-methylamines such as codeine, thebaine, and oripavine. These substrates are readily N-demethylated under mild conditions, employing sub-stoichiometric amounts of the substituted ferrocene at ambient temperature. These reactions are equally efficient in air and may also be carried out in one pot. Georg Thieme Verlag Stuttgart · New York.