Literature DB >> 14656122

Efficient N-demethylation of opiate alkaloids using a modified nonclassical Polonovski reaction.

Kristy McCamley1, Justin A Ripper, Robert D Singer, Peter J Scammells.   

Abstract

A modified Polonovski reaction has been employed to N-demethylate several opiate alkaloids in moderate to high yield. This method provides an alternative to traditional N-demethylation procedures which utilize toxic reagents such as cyanogen bromide or expensive reagents such as vinyl chloroformate. The current synthesis involves N-oxide formation, isolation of the corresponding N-oxide hydrochloride, and an FeSO(4).7H(2)O mediated Polonovski reaction to afford the desired secondary amine.

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Year:  2003        PMID： 14656122     DOI： 10.1021/jo035243z

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

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Review 4.  N-Dealkylation of Amines.

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6.  Asymmetric synthesis of (-)-naltrexone.

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7.  An organophotocatalytic late-stage N-CH3 oxidation of trialkylamines to N-formamides with O2 in continuous flow.

Authors:  Mark John P Mandigma; Jonas Žurauskas; Callum I MacGregor; Lee J Edwards; Ahmed Shahin; Ludwig d'Heureuse; Philip Yip; David J S Birch; Thomas Gruber; Jörg Heilmann; Matthew P John; Joshua P Barham
Journal:  Chem Sci       Date:  2021-12-28       Impact factor: 9.825

8.  Organophotocatalytic N-Demethylation of Oxycodone Using Molecular Oxygen.

Authors:  Yuesu Chen; Gabriel Glotz; David Cantillo; C Oliver Kappe
Journal:  Chemistry       Date:  2020-02-18       Impact factor: 5.236
  8 in total

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