Monatshefte für Chemie / Chemical Monthly

, Volume 128, Issue 12, pp 1247–1254 | Cite as

1,3-Diphenylpropane-1,3-diamines XI. Conversion of a 3-hydroxy-1,3-diphenylpropan-1-one to 1,3-diphenylpropane-1,3-diamines

  • A. Kaiser
  • P. Bielmeier
  • W. Wiegrebe
Organische Chemie Und Biochemie


Highly diastereoselective BH3/THF syn-reduction of the 3-hydroxy-1,3-diphenylpropan-1-one/BBr3 complex3/BBr3 (cf.Sarko) afforded themeso-diol4, whereas racemate5 was obtained by BH3/THF reduction without complexation. Mesylation, exchange of mesylate by azide, and reduction with SnCl2/thiophenol led to the diamines10 and11 which were also produced by reductive N-N cleavage of the 4,5-dihydropyrazole13.


1,3-Diphenylpropane-1,3-diamines 3-Hydroxy-1,3-diphenylpropan-1-one 3,5-Diphenyl-4,5-dihydropyrazole syn-Reduction of β-hydroxyketones 

1,3-Diphenylpropan-1,3-diamine, 11. Mitt.: Umsetzung eines 3-Hydroxy-1,3-diphenylpropan-1-ons zu 1,3-Diphenylpropan-1,3-diaminen


Hochdiastereoselektive BH3/THF-syn-Reduktion des 3-Hydroxy-1,3-diphenylpropan-3-on/BBr3-Komplexes3/BBr3 (vergl.Sarko) lieferte dasmeso-Diol4, wähend das Razemat5 durch BH3/THF-Reduktion ohne Komplexbildung entstand. Mesylierung, Ersatz von Mesylat durch Azid und SnCl2/Thiophenol-Reduktion führte zu den Diaminen10 und11, die auch durch reduktive N-N-Spaltung aus dem 4,5-Dihydropyrazol13 erhalten wurden.


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Copyright information

© Springer-Verlag 1997

Authors and Affiliations

  • A. Kaiser
    • 1
  • P. Bielmeier
    • 1
  • W. Wiegrebe
    • 1
  1. 1.Institute of PharmacyUniversity of RegensburgRegensburgGermany

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