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Monatshefte für Chemie / Chemical Monthly

, Volume 123, Issue 5, pp 435–441 | Cite as

Morphine alkaloids, part 114. A stereohomogeneous synthesis of N-demethyl-N-substituted-14-hydroxydihydromorphines

  • Sándor Hosztafi
  • Sándor Berenyi
  • Géza Tóth
  • Sándor Makleit
Organische Chemie Und Biochemie

Summary

A new route for the stereohomogeneous synthesis of N-demethyl-N-substituted-14-hydroxydihydromorphines2 a – f has been elaborated, involving O-demethylation of the novel dihydrocodeine derivatives6 a – f, obtained upon alkylation of the hitherto unknown N-demethyl-14-hydroxydihydrocodeine (5).

Keywords

6α,14β-Diacetoxy-4,5α-epoxy-3-methoxy-17-methyl-morphinan, N-demethylation of 3,6α,14β-Triacetoxy-17-alkyl-4,5α-epoxymorphinan, N-demethylation of 17-Alkyl-4,5α-epoxy-6α,14β-dihydroxy-3-methoxymorphinan, O-demethylation of 4,5α-Epoxy-6α,14β-dihydroxy-3-methoxymorphinan, N-alkylation of 

Synthese von N-Demethyl-N-Substituierten-14-Hydroxydihydromorphinen in stereochemisch einheitlicher Form

Zusammenfassung

Es wurde ein neuer Weg für die Darstellung von N-Demethyl-N-Substituierten-14-Hydroxydihydromorphinen2 a – f in stereochemisch einheitlicher Form ausgearbeitet. Diese erfolgte durch die O-Demethylierung der neuen Dihydrocodein-Derivate6 a – f, die durch N-Alkylierung des neuen N-Demethyl-14-hydroxycodeins hergestellt wurden.

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References

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Copyright information

© Springer-Verlag 1992

Authors and Affiliations

  • Sándor Hosztafi
    • 1
  • Sándor Berenyi
    • 2
  • Géza Tóth
    • 3
  • Sándor Makleit
    • 2
  1. 1.Alkaloida Chemical FactoryTiszavasváriHungary
  2. 2.Department of Organic ChemistryKossuth Lajos University of DebrecenDebrecenHungary
  3. 3.Isotope Laboratory of the Hungarian Academy of SciencesSzegedHungary

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