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508-54-3Relevant academic research and scientific papers
A simple and practical method for the oxidation of thebaine to 14-hydroxycodeinone by V2O5-H2O2
Sharma, Saikat Das,Konwar, Dilip
, p. 1062 - 1064 (2009)
An efficient, practical and expeditious method has been developed for the oxidation of thebaine to 14-hydroxycodeinone in excellent yield by employing 20 mol% of V2O5 in the presence of 30% H2O 2 in aqueous medium. The method provides a clean technological process for the preparation of a key drug intermediate, 14-hydroxycodeinone. Georg Thieme Verlag Stuttgart.
Preparation of 8-Alkyl-14-hydroxydihydrocodeinones
Leland, David L.,Polazzi, Joseph O.,Kotick, Michael P.
, p. 4012 - 4014 (1981)
Reaction of 14-codeinone (1b) with lithium dimethylcuprate gave a 2:1 isomeric mixture of the corresponding 8α-methyl (2) and 8β-methyl (3) 14-(trimethylsilyl)oxydihydro derivatives.Selective removal of the silyl group from α isomer 2 to give 4, by use of silica gel, allowed resolution of the mixture. 8β-Methyl-14-hydroxydihydrocodeinone (5) was prepared from 3 by cleavage of the silyl ether with n-Bu4NF.Treatment of 14-hydroxycodeinone with Me2CuLi gave a 4:1 mixture of alkylated products 4 and 5.The (tert-butyldimethylsilyl)oxy ether 1c under similar conditions gave exclusively the stable 8α isomer 6.Reaction of trimethylsilyl compound 1b with Et2CuLi or n-Bu2CuLi gave approximately equal amounts of the corresponding 8-alkyl 14-O-silylated isomers.These results are in contrast to previous work with codeinone which demonstrated that lithium organocopper reagents add almost exclusively to the β face of "T-shaped" morphinone derivatives.
Studies into the direct oxidation of codeinone to 14-hydroxycodeinone
Coop, Andrew,Rice, Kenner C.
, p. 11429 - 11436 (1999)
The direct oxidation of codeinone (5) to 14-hydroxycodeinone (6) was investigated with a wide range of oxidizing agents. The majority of reagents gave little or no desired product. Peracids were found to be moderately successful, with dimethyl peracetic acid giving the greatest yield (37%). Metallic oxidants generally gave rise to competing oxidations, however Co(AcO)3 was found to conveniently oxidize 5 to 6 in 51% yield, representing a practical, non-chromatographic procedure for the preparation of 14- hydroxycodeinone.
14-Hydroxylation of opiates: Catalytic direct autoxidation of codeinone to 14-hydroxycodeinone
Zhang, Qibo,Rich, Joseph O.,Cotterill, Ian C.,Pantaleone, David P.,Michels, Peter C.
, p. 7286 - 7287 (2005)
Codeinone (3) was efficiently and directly converted to 14-hydroxycodeinone (1) by catalytic air oxidation in aqueous solution. A number of simple manganese and copper salts were identified to be effective catalysts, including MnSO4, KMnO4, and CuSO4. An appropriate reducing agent, such as sodium thiosulfate, is required in the reaction mixture presumably for the reduction of a detrimental peroxide intermediate. This discovery allows the more abundant codeine to be employed as the starting material for the synthesis of 14-hydroxylated opiate drugs without recourse to a thebaine-like intermediate. These discoveries were inspired from our study of microbial transformation of codeine to 14-hydroxycodeine by Mycobacterium neoaurum, where we found the actual 14-hydroxylation step is a chemical reaction rather than an enzymatic reaction, as previously believed. Copyright
Method for preparing oxycodone hydrochloride impurity B
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Paragraph 0029-0032, (2021/10/13)
The invention belongs to the field of chemical engineering, and particularly relates to a preparation method of oxycodone hydrochloride impurity B. To the method, 14 - hydroxycodeinone is taken as a raw material, impurities Michael are obtained through B addition reaction under basic conditions, the method is simple and easy to operate, and the product purity is high. The yield is high, and can be used for researching the quality of oxycodone hydrochloride.
PROCESSES FOR PREPARING NOR-OPIOID COMPOUNDS AND OPIOID ANTAGONISTS BY ELECTROCHEMICAL N-DEMETHYLATION
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Page/Page column 26, (2021/12/31)
The present invention relates to a process for preparing a nor-opioid compound wherein an opioid precursor compound is electrochemically N-demethylated. The present invention further relates to a process for preparing an opioid antagonist compound, wherein an opioid precursor compound is electrochemically N-demethylated and the thus obtained nor-opioid compound is alkylated again at its secondary amine functional group.
Electrochemical N-Demethylation of 14-Hydroxy Morphinans: Sustainable Access to Opioid Antagonists
Cantillo, David,Glotz, Gabriel,Kappe, C. Oliver
supporting information, p. 6891 - 6896 (2020/09/15)
The most challenging step in the preparation of many opioid antagonists is the selective N-demethylation of a 14-hydroxymorphinan precursor. This process is carried out on a large scale using stoichiometric amounts of hazardous chemicals like cyanogen bromide or chloroformates. We have developed a mild reagent- and catalyst-free procedure for the N-demethylation step based on the anodic oxidation of the tertiary amine. The ensuing intermediates can be readily hydrolyzed to the target nor-opioids in very good yields.
PROCESS FOR IMPROVED OXYCODONE SYNTHESIS
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Paragraph 0615-0638, (2017/02/24)
Processes for preparing oxycodone are provided. Said processes encompass a step which is a hydrogenation of an 14-hydroxycodeinone salt in the presence of trifluoroacetic acid and/or a glycol.
Processes for Making Opioids Including 14-Hydroxycodeinone and 14-hydroxymorphinone
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Paragraph 0109; 0110, (2016/03/14)
Improved processes for making opioid products having low impurity levels including making 14-hydroxycodeinone and 14-hydroxymorphinone from thebaine and oripavine, respectively.
PROCESS FOR THE PREPARATION OF OXYMORPHONE FREEBASE
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Page/Page column 55-56, (2016/12/12)
The present invention is directed to a process for the preparation oxymorphone freebase, comprising hydrogenation of 14-hydroxymorphinone in DMF, to yield oxymorphone freebase, preferably oxymorphone freebase of improved appearance, purity and / or yield. The present invention is further directed to oxymorphone freebase with improved impurity profile. The present invention is further directed to an HPLC or UPLC system/method for analysis of opioid compounds.