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33522-95-1Relevant articles and documents
Batch- and Continuous-Flow Aerobic Oxidation of 14-Hydroxy Opioids to 1,3-Oxazolidines—A Concise Synthesis of Noroxymorphone
Gutmann, Bernhard,Weigl, Ulrich,Cox, D. Phillip,Kappe, C. Oliver
, p. 10393 - 10398 (2016)
14-Hydroxymorphinone is converted to noroxymorphone, the immediate precursor of important opioid antagonists, such as naltrexone and naloxone, in a three-step reaction sequence. The initial oxidation of the N-methyl group in 14-hydroxymorphinone with in situ generated colloidal palladium(0) as the catalyst and molecular oxygen as the terminal oxidant constitutes the key transformation in this new route. This oxidation results in the formation of an unexpected oxazolidine ring structure. Subsequent hydrolysis of the oxazolidine under reduced pressure followed by hydrogenation in a packed-bed flow reactor using palladium(0) as the catalyst provides noroxymorphone in high purity and good overall yield. To overcome challenges associated with gas–liquid reactions with molecular oxygen, the key oxidation reaction was translated to a continuous-flow process.
Efficient Synthesis of 14-Hydroxymorphinans from Codeine
Schwartz, Martin A.,Wallace, Rebecca A.
, p. 1525 - 1528 (1981)
Codeine is converted to 7,8-dihydro-14-hydroxynorcodeinone (noroxycodone) in six steps and 52percent overall yield or to noroxymorphone in seven steps and 43percent overall yield.N-Demethylation and oxidation of codeine afford N-(ethoxycarbonyl)norcodeinone, which is converted to its dienol acetate derivative and oxidized with singlet oxygen to give N-(ethoxycarbonyl)-14-hydroxynorcodeinone in the key step.Hydrogenation of the latter affords N-(ethoxycarbonyl)noroxycodone, which upon acid hydrolysis yields noroxycodone.Alternatively, O-demethylation of N-(ethoxycarbonyl)noroxycodone with boron tribromide and subsequent acid hydrolysis gives noroxymorphone.The results of the singlet oxygen oxidation of the pyrrolidine dienamine derived from N-(ethoxycarbonyl)norcodeinone are also described.
An improved synthesis of noroxymorphone
Ninan,Sainsbury
, p. 6709 - 6716 (1992)
A brief synthesis of noroxymorphone is described which involves the oxidation of 3-O-(t)butyldimethylsilylmorphine by manganese dioxide. The initial product is the corresponding morphinone which is further oxidised to the 14-hydroxymorphinone. After hydrogenation the 7,8-dihydro-14-hydroxymorphinone is acetylated and N-demethylation of the 14-O-acetylated product is achieved using vinyl chloroformate as the reagent. The overall yield from morphine is 40-45%.
Synthesis and Characterization of Azido Aryl Analogs of IBNtxA for Radio-Photoaffinity Labeling Opioid Receptors in Cell Lines and in Mouse Brain
Grinnell, Steven G.,Uprety, Rajendra,Varadi, Andras,Subrath, Joan,Hunkele, Amanda,Pan, Ying Xian,Pasternak, Gavril W.,Majumdar, Susruta
, p. 977 - 993 (2020/05/29)
Mu opioid receptors (MOR-1) mediate the biological actions of clinically used opioids such as morphine, oxycodone, and fentanyl. The mu opioid receptor gene, OPRM1, undergoes extensive alternative splicing, generating multiple splice variants. One type of splice variants are truncated variants containing only six transmembrane domains (6TM) that mediate the analgesic action of novel opioid drugs such as 3′-iodobenzoylnaltrexamide (IBNtxA). Previously, we have shown that IBNtxA is a potent analgesic effective in a spectrum of pain models but lacks many side-effects associated with traditional opiates. In order to investigate the targets labeled by IBNtxA, we synthesized two arylazido analogs of IBNtxA that allow photolabeling of mouse mu opioid receptors (mMOR-1) in transfected cell lines and mMOR-1 protein complexes that may comprise the 6TM sites in mouse brain. We demonstrate that both allyl and alkyne arylazido derivatives of IBNtxA efficiently radio-photolabeled mMOR-1 in cell lines and MOR-1 protein complexes expressed either exogenously or endogenously, as well as found in mouse brain. In future, design and application of such radio-photolabeling ligands with a conjugated handle will provide useful tools for further isolating or purifying MOR-1 to investigate site specific ligand–protein contacts and its signaling complexes.
PROCESS FOR THE PREPARATION OF MORPHINANE COMPOUNDS
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Page/Page column 9, (2019/01/21)
The invention describes the process of catalytic O-demethylation of 3-methoxy-morphinane compounds using boron tribromide. Addition of catalysts reduces the reaction time, improves reacting the substrate to give the product in very good purity and yield. The said approach can be used, for example, for the preparation of oxymorphone, naltrexone, naloxone and nalbuphine from their respective O-methyl derivatives.