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125-29-1Relevant articles and documents
Studies on regioselective hydrogenation of thebaine and its conversion to hydrocodone
Leisch, Hannes,Carroll, Robert J.,Hudlicky, Tomas,Cox, D. Phillip
, p. 3979 - 3981 (2007)
Thebaine was subjected to catalytic hydrogenation under a variety of conditions in order to determine the regioselectivity for C-6/C-7 versus C-8/C-14 olefin saturation.
Selective Olefin Reduction in Thebaine Using Hydrazine Hydrate and O2 under Intensified Continuous Flow Conditions
Pieber, Bartholom?us,Cox, D. Phillip,Kappe, C. Oliver
, p. 376 - 385 (2016)
Hydrocodone, a high value active pharmaceutical ingredient (API), is usually produced in a semisynthetic pathway from morphine, codeine or thebaine. The latter alkaloid is an attractive precursor as it is not used as a remedy itself. The key step in this production route is a selective olefin reduction forming 8,14-dihydrothebaine which can be subsequently hydrolyzed to yield hydrocodone. Unfortunately, standard hydrogenation procedures cannot be applied due to severe selectivity problems. A transfer hydrogenation using in situ generated diimide is the only known alternative to achieve a selective transformation. The most (atom) economic generation of this highly unstable reducing agent is by oxidizing hydrazine hydrate (N2H4·H2O) with O2. In the past, this route was "forbidden" on an industrial scale due to its enormous explosion potential in batch. A continuous high-temperature/high-pressure methodology allows an efficient, safe, and scalable processing of the hazardous reaction mixture. The industrially relevant reduction was achieved by using four consecutive liquid feeds (of N2H4·H2O) and residence time units, resulting in a highly selective reduction within less than 1 h.
One-pot conversion of thebaine to hydrocodone and synthesis of neopinone ketal
Carroll, Robert J.,Leisch, Hannes,Rochon, Lena,Hudlicky, Tomas,Cox, D. Phillip
, p. 747 - 752 (2009)
The ethylene glycol ketal of neopinone was prepared in a one-pot procedure by the reaction of thebaine with ethylene glyocol in the presence of p-toluenesulfonic acid. The ketal is also an intermediate in the conversion of thebaine to hydrocodone with ethylene glycol and Pd(OAc)2, followed by hydrogenation. Additionally, a one-pot procedure for the conversion of thebaine to hydrocodone was achieved by employing palladium catalysis in aqueous medium. Palladium serves a dual purpose in this transformation, first for the activation of the dienol ether of thebaine and second as a hydrogenation catalyst. This procedure was found to be comparable to the two-step protocol which employs diimide reduction of thebaine followed by acid-catalyzed hydrolysis of the resulting 8,14-dihydrothebaine to hydrocodone. Experimental and spectral data are provided for all compounds.
14,17-Cyclonorcodeinone dimethylacetal: A New Codeinon Derivative, II
Fleischhacker, W.,Richter, B.,Voellenkle, H.
, p. 399 - 411 (1991)
In addition to a short communication describing the synthesis of 14,17-cyclonorcodeinone dimethylacetal 1a we wish to present a simple alternative route together with a selection of some reactions depending on the great reactivity of this highly strained small ring system.The structure of 1a is established by X-ray analysis.
Transition metal-catalyzed redox isomerization of codeine and morphine in water
Gomez, Antonio Bermejo,Holmberg, Paer,Baeckvall, Jan-E.,Martin-Matute, Belen
, p. 39519 - 39522 (2014)
A water-soluble rhodium complex formed from commercially available [Rh(COD)(CH3CN)2]BF4 and 1,3,5-triaza-7- phosphaadamantane (PTA) catalyzes the isomerization of both codeine and morphine into hydrocodone and hydromorphone with very high efficiency. The reaction is performed in water, allowing isolation of the final products by simple filtration, which results in very high isolated yields. The reactions can be easily scaled up to 100 g.
NOVEL OPIOID COMPOUNDS AND USES THEREOF
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Paragraph 0509-0511, (2019/09/12)
This invention relates to novel opioid derivatives of Formula I: or a pharmaceutically acceptable salt or solvate thereof, wherein R1, R3, R4 and Z are as defined herein in the disclosure. The invention also relates to the use of such compounds for the treatment or prevention of, for example, pain.
PROCESS FOR THE PREPARATION OF BENZHYDROCODONE HYDROCHLORIDE
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Paragraph 0190-0191, (2018/03/25)
The invention is directed to processes for the preparation of benzhydrocodone hydrochloride. More particularly, the invention is directed to processes for a one-pot synthesis of benzhydrocodone hydrochloride of improved yield and/or purity.
SUPPORTED METAL CATALYST FOR THE PRODUCTION OF HYDROCODONE AND HYDROMORPHONE
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Page/Page column 7, (2018/01/15)
The present invention relates to the process for the manufacture of hydrocodone or hydromorphone from their enol derivatives codeine and morphine respectively. Particularly, the invention discloses a metal catalyst that is used in low amount, leads to high yields and can easily be reused.
General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand
Erbing, Elis,Vázquez-Romero, Ana,Bermejo Gómez, Antonio,Platero-Prats, Ana E.,Carson, Fabian,Zou, Xiaodong,Tolstoy, P?ivi,Martín-Matute, Belén
supporting information, p. 15659 - 15663 (2016/10/25)
Remarkably simple IrIIIcatalysts enable the isomerization of primary and sec-allylic alcohols under very mild reaction conditions. X-ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*IrIII], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.
PREPARATION OF SATURATED KETONE MORPHINAN COMPOUNDS BY CATALYTIC ISOMERISATION
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Page/Page column 46-47; 49-51, (2015/02/19)
There is provided a novel process for the preparation of a compound of formula I, wherein R1, R2 and R3 are as described in the description, by conversion of a corresponding allylic alcohol.