Advertisement

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

Summary

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.

Keywords

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

Zusammenfassung

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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    Part X: Bielmeier P, Kaiser A, Gust R, Wiegrebe W (1996) Monatsh Chem127: 1073Google Scholar
  2. [2]
    von Auwers K, Müller H (1933) J Prakt Chem NF137: 57Google Scholar
  3. [3]
    Kammermeier T, Kaiser A, Lee GS, Burgemeister T, Wiegrebe W (1991) Arch Pharm (Weinheim)324: 177Google Scholar
  4. [4]
    Smith AB, Levenberg PA (1981) Synthesis 567Google Scholar
  5. [5]
    Karl J, Gust R, Spruss T, Schneider RM, Schönenberger H, Engel J, Wrobel K-H, Lux F, Trebert-Haeberlin S (1988) J Med Chem31: 72Google Scholar
  6. [6]
    Itsuno S, Hirao A, Nakahama S, Yamazaki N (1983) J Chem Soc Perkin Trans 1, 1673Google Scholar
  7. [7]
    Sarko CR, Collibee SE, Knorr AL, DiMare M (1996) J Org Chem61: 868Google Scholar
  8. [8]
    Kammermeier T, Wiegrebe W (1994) Arch Pharm (Weinheim)327: 697Google Scholar
  9. [9]
    Roos GHP, Donovan AR (1996) Synlett 1189Google Scholar
  10. [10]
    Crossland RK, Servis KL (1970) J Org Chem35: 3195Google Scholar
  11. [11]
    Wiley RH, Moffat J (1957) J Org Chem22: 995Google Scholar
  12. [12]
    Eliel EL (1956) In: Newman MS (ed) Steric Effects in Organic Chemistry. Wiley, New York, p 68Google Scholar
  13. [13]
    Batra M, Romea P, Urpi F, Vilarrasa J (1990) Tetrahedron46: 587Google Scholar

Copyright information

© Springer-Verlag 1997

Authors and Affiliations

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

Personalised recommendations