Investigation of the acid-catalyzed rearrangement of morphinans

Csaba Csutorás, Sándor Berényi, John L. Neumeyer

Research output: Contribution to journalArticle

3 Citations (Scopus)


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
Issue number6
Publication statusPublished - Sep 1 2007


  • Acid-catalyzed rearrangement
  • Codeine
  • Morphinans
  • Morphine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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