Direct reductive amination of aldehyde bisulfite adducts induced by 2-picoline borane: application to the synthesis of a DPP-IV inhibitor

J Org Chem. 2013 Feb 15;78(4):1655-9. doi: 10.1021/jo3023878. Epub 2013 Jan 24.

Abstract

Aldehyde-bisulfite adducts dervied from unstable parent aldehydes were reductively alkylated in a direct fashion with a variety of amines. This approach features the use of 2-picoline borane as the reducing agent and a protic solvent for the reaction media and has been successfully applied to the synthesis of a DPP-IV inhibitor and a variety of other amines.

MeSH terms

  • Aldehydes
  • Alkylation
  • Amination
  • Amines / chemistry*
  • Boranes / chemistry
  • Dipeptidyl Peptidase 4 / agonists*
  • Dipeptidyl Peptidase 4 / chemistry*
  • Morpholines / chemistry*
  • Picolines / chemistry*
  • Sulfites / chemistry*

Substances

  • Aldehydes
  • Amines
  • Boranes
  • Morpholines
  • Picolines
  • Sulfites
  • Dipeptidyl Peptidase 4