The Preparation of Some Dihydro Ketones in the Morphine Series by Oppenauer Oxidation

Rapoport, Henry; Naumann, R.W.; Bissell, Eugene R.; Bonner, Robert M.

doi:10.1021/jo01151a029

Cited by 64 publications

(34 citation statements)

References 11 publications

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“…3-Deoxymorphine (13). A solution of 3.10 g (9.54 mmol) of 12 in 30 mL of dry T H F was added dropwise, with stirring, to a slurry of 3.63 g (95.4 mmol) of LiAlH, in 90 mL of THF under argon.…”

Section: Reden Et Almentioning

confidence: 99%

Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions

Reden¹,

Reich²,

Rice³

et al. 1979

J. Med. Chem.

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Several 3-deoxy opioids and 3,6-dideoxydihydromorphine was synthesized to ascertain the effect of the phenolic hydroxyl group on antinociceptive potency and receptor binding affinity. Catalytic reduction of the 3-tetrazolyl ether derivatives of dihydromorphine provided the entry into the 3-deoxydihydro series. The prototype, 3-deoxymorphine, was prepared by lithium aluminum hydride reduction of 3-deoxy-N-carbethoxymorphinone, obtained via its 7-(phenylseleno) derivative. 3-Deoxydihydromorphinone and 3,6-dideoxydihydromorphine were found to be about as potent as, or more potent than, morphine in standard antiociceptive assays. Each of them, however, was less potent than the comparable 3-hydroxy analogue, and their binding affinity to the opiate receptor was substantially decreased. The epoxy ring in 3.6-dideoxydihydromorphine was found to increase the antinociceptive potency of the compound.

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Section: Reden Et Almentioning

confidence: 99%

Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions

Reden¹,

Reich²,

Rice³

et al. 1979

J. Med. Chem.

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“…Codeinone dimethyl ketal (9) was obtained in the reaction of 8,14-dihydrothebaine (10) and methyl hypobromide and then as a second step the dehydrobromination of the 7-bromo-dihydrocodeinone dimethyl ketal (11) by potassium tamylate. Compound 10 was easily prepared from codeine (3) via dihydrocodeinone [35,36].…”

Section: Synthetic Routes To Thebainementioning

confidence: 99%

Recent Developments in the Chemistry of Thebaine and its Transformation Products as Pharmacological Targets

Berényi¹,

Csutorás²,

Sipos

2009

CMC

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The most practical synthetic routes to the preparation of as important pharmaceuticals as oxycodone, naloxone, naltrexone, nalbuphine and buprenorphine have utilized the alkaloid, thebaine, as a starting material. This review intends to focus on chemical transformations of morphinans which resulted in morphinandiene derivatives with well-established and novel pharmacological potencies. These chemical transformations were mainly associated with the formation and substitution of the unique diene structure of the ring C of the morphinan backbone.

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“…Alternative oxidants are cyclohexanone with aluminium tri(terf-butoxide) or aluminium triphenoxide (Rapoport, 1950;Pfister and Tishler (Merck & Co), 1955;Kleemann et al, 1999). Alternative oxidants are cyclohexanone with aluminium tri(terf-butoxide) or aluminium triphenoxide (Rapoport, 1950;Pfister and Tishler (Merck & Co), 1955;Kleemann et al, 1999).…”

Section: Hydromorphonementioning

confidence: 99%

Opioids: 3.4 Opioids with Clinical Relevance

Friderichs

Buschmann

2002

Analgesics

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The Preparation of Some Dihydro Ketones in the Morphine Series by Oppenauer Oxidation

Cited by 64 publications

References 11 publications

Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions

Deoxymorphines: role of the phenolic hydroxyl in antinociception and opiate receptor interactions

Recent Developments in the Chemistry of Thebaine and its Transformation Products as Pharmacological Targets

Opioids: 3.4 Opioids with Clinical Relevance

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