The Preparation of Morphine-N-methyl-C<sup>14</sup>

Rapoport, Henry; Lovell, Calvin H.; Tolbert, Bert M.

doi:10.1021/ja01156a543

Cited by 33 publications

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“…Figures in parentheses arc tin: 05% confidence limits. At dose levels near the 1 (1, 50. and 84%, response, 20 25 mice per does level were used. At other dose levels, 10 15 mice per dose level were used.…”

Section: Resultsmentioning

confidence: 99%

Some Aspects of the Fate and Relationship of the N-Methyl Group of Morphine to its Pharmacological Activity^1a

Elison¹,

Elliott²,

Look³

et al. 1963

J. Med. Chem.

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Fate and Relationship of N-Methyl to Activity of Morphine 237 This material gelled in most organic solvents, but was recrystallized from about 5 1. of dioxane 3 times and once from 3.5 1. of chloroform to obtain white waxy crystals, m.p. 120-122°. Other close analogs showed the same tendency to gel in most organic solvents at conventional concentrations.Acknowledgments.-We are grateful to Dr. D. B. Seeley for the fermentative preparation of the epoxy-succinic acid, to Dr. S. Y. P'an for measuring hypnotic activities, to Joseph Kaiser for toxicity determinations, to Dr. Arthur English for the antifungal tests, and to Charles Scott for technical assistance. Insecticide tests were done at the Wisconsin Alumni Research Foundation.

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Section: Resultsmentioning

confidence: 99%

Some Aspects of the Fate and Relationship of the N-Methyl Group of Morphine to its Pharmacological Activity^1a

Elison¹,

Elliott²,

Look³

et al. 1963

J. Med. Chem.

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“…The structure of the ketal (7) was confirmed by single crystal x-ray diffraction analysis. Then, hydrolysis of the ketal with aqueous hydrogen chloride yielded the corresponding ketone and generation of the potassium enol of the latter with potassium bis(trimethylsilyl)amide in THF at -78 o C followed by oxaziridine oxidation produced the acyloin (8) in 70 -88% yield as shown in Fig.…”

Section: Fig (3)mentioning

confidence: 97%

Syntheses of Morphine and Codeine (1992‐2002): Templates for Exploration of Synthetic Tools

2006

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“…Finally, codeine (2 ) was obtained from the 1bromocodeinone by reduction with lithium aluminum hydride (LiAlH 4 ) in THF in about 30% yield and demethylation to morphine (1) itself effected (in 34% yield) by reaction with pyridinium hydrochloride -the procedure pioneered by Henry Rapoport, Calvin H. Lovell and Bert M. Tolbert [7].…”

Section: : Marcus a Tius And Michael A Kerr [5]mentioning

confidence: 99%

Syntheses of Morphine and Codeine (1992 - 2002): Templates for Exploration of Synthetic Tools

Mascavage¹,

Wilson²,

Dalton³

2006

COS

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Morphine (1) and its O-methylated analogue codeine (2), analgesic alkaloids of the opium poppy (Papaver Somniferium), have been targets of organic chemists engaged in synthetic activities for at least half a century. The "first" (Gates) and "most efficient" (Rice) syntheses of morphine (1) and codeine (2) are well known and have been reviewed and analyzed extensively numerous times. However, syntheses of the same two alkaloids that have been reported since 1992 and which have been used as devices to advance the art of organic synthesis are not as widely recognized and they have not been as thoroughly reviewed. Here they are analyzed in the spirit of the use of these two compounds as templates. Further, since both racemic and enantiospecific syntheses are important and since all eight (8) approaches (since 1992) are sufficiently different so as to warrant more tha n superficial examination, they are all considered.

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The Preparation of Morphine-N-methyl-C¹⁴

Cited by 33 publications

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Some Aspects of the Fate and Relationship of the N-Methyl Group of Morphine to its Pharmacological Activity^1a

Some Aspects of the Fate and Relationship of the N-Methyl Group of Morphine to its Pharmacological Activity^1a

Syntheses of Morphine and Codeine (1992‐2002): Templates for Exploration of Synthetic Tools

Syntheses of Morphine and Codeine (1992 - 2002): Templates for Exploration of Synthetic Tools

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The Preparation of Morphine-N-methyl-C14

Cited by 33 publications

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Some Aspects of the Fate and Relationship of the N-Methyl Group of Morphine to its Pharmacological Activity1a

Some Aspects of the Fate and Relationship of the N-Methyl Group of Morphine to its Pharmacological Activity1a

Syntheses of Morphine and Codeine (1992‐2002): Templates for Exploration of Synthetic Tools

Syntheses of Morphine and Codeine (1992 - 2002): Templates for Exploration of Synthetic Tools

Contact Info

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The Preparation of Morphine-N-methyl-C¹⁴

Some Aspects of the Fate and Relationship of the N-Methyl Group of Morphine to its Pharmacological Activity^1a

Some Aspects of the Fate and Relationship of the N-Methyl Group of Morphine to its Pharmacological Activity^1a