Investigation of the acid-catalyzed rearrangement of morphinans

Csaba Csutorás, Sándor Berényi, John L. Neumeyer

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The acid-catalyzed rearrangement of morphine (1), codeine (3), 3-deoκynormorphine (14) and N-cyclopropylmethyl-3-deoxynormorphine (11) was investigated with methanesulfonic acid. The yield in the reangement reaction was significantly improved using milder reaction conditions, compared to the earlier reported methods. As an evidence for the mechanism of the acid-catalyzed rearrangement of morphinans, the diene intermediate 13 was isolated. A new method, using boron trifluoride etherate was elaborated for the rearrangement of morphinandieries.

Original languageEnglish
Pages (from-to)409-413
Number of pages5
JournalLetters in Organic Chemistry
Volume4
Issue number6
DOIs
Publication statusPublished - Sep 1 2007

Keywords

  • Acid-catalyzed rearrangement
  • Codeine
  • Morphinans
  • Morphine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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