Download PDF
Synthesis 2009(10): 1757-1759  
DOI: 10.1055/s-0028-1088046
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

An Inexpensive Procedure for Reductive Aminations Using Dimethylamineborane on Millimolar and Molar Scale

Regina Ortmann, Martin Schlitzer*
Institute of Pharmaceutical Chemistry, Philipps Universität Marburg, Marbacher Weg 6, 35032 Marburg, Germany
Fax: +49(6421)2825953; e-Mail: Schlitzer@staff.uni-marburg.de;
Further Information

Publication History

Received 23 January 2009
Publication Date:
14 April 2009 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

We have developed an inexpensive and easy procedure for reductive aminations using dimethylamineborane instead of cyanoborohydride­. Dimethylamineborane is easily prepared from readily available inexpensive starting materials and can be used without isolation even on molar scale.

Key words

amines - aminations - hydrides - imines - medicinal chemistry

    References

  • 1a Greenwood B. Mutabingwa T. Nature  2002,  415:  670 
    Search in Google Scholar
  • 1b Ridley RG. Nature  2002,  415:  686 
    Search in Google Scholar
  • 1c Schlitzer M. ChemMedChem  2007,  2:  944 
    Search in Google Scholar
  • 1d Schlitzer M. Arch. Pharm. (Weinheim, Ger.)  2008,  341:  149 
    Search in Google Scholar
  • 2a Borrmann S. Adegnika AA. Matsiegui P.-B. Issifou S. Schindler A. Mawilli-Mboumbe DP. Baranek T. Wiesner J. Jomaa H. Kremsner PG. J. Infect. Dis.  2004,  189:  901 
    Search in Google Scholar
  • 2b Borrmann S. Issifou S. Esser G. Adegnika AA. Ramharter M. Matsiegui P.-B. Oyakhirome S. Mawilli-Mboumbe DP. Missimou MA. Kun JFJ. Jomaa H. Kremsner PG. J. Infect. Dis.  2004,  190:  1534 
    Search in Google Scholar
  • 2c Borrmann S. Lundgren I. Oyakhirome S. Impouma B. Matsiegui P.-B. Adegnika AA. Issifou S. Kun HFJ. Hutchinson D. Wiesner J. Jomaa H. Kremsner PG. Antimicrob. Agents Chemother.  2006,  2713 
  • 2d Oyakhirome S. Issifou S. Bongratz P. Barondi F. Ramharter M. Kun JF. Missinou MA. Lell B. Kremsner PG. Antimicrob. Agents Chemother.  2007,  1869 
  • 3 Wiesner J. Borrmann S. Jomaa H. Parasitol. Res.  2003,  90:  71 
    CrossrefSearch in Google Scholar
  • 4a Kurz T. Geffken D. Wackendorff C. Z. Naturforsch., B  2002,  58:  106 
    Search in Google Scholar
  • 4b Ortmann R. Wiesner J. Reichenberg A. Henschker D. Beck E. Jomaa H. Schlitzer M. Arch. Pharm. Chem. Life Sci.  2005,  338:  305 
    Search in Google Scholar
  • 4c Ortmann R. Wiesner J. Silber K. Klebe G. Jomaa H. Schlitzer M. Arch. Pharm. Chem. Life Sci.  2007,  340:  483 
    Search in Google Scholar
  • 4d Perruchon J. Ortmann R. Schlitzer M. Synthesis  2007,  3553 
  • 5 Hutchins RO. Learn K. Nazer B. Pytlewski D. Org. Prep. Proced. Int.  1984,  16:  335 
    CrossrefSearch in Google Scholar
  • 6 Iwasaki Y. inventors; Shirol Yakuhin Co., Ltd., US Patent 006060623  A.  ; Chem. Abstr. 2000, 132, 293877
7

Manuscript in preparation.