An application of borane as a protecting group for pyridine

J Org Chem. 2008 Sep 5;73(17):6899-901. doi: 10.1021/jo801040m. Epub 2008 Aug 5.

Abstract

Efforts to couple 4 with 12 employing base mediation are problematic due to the formation of 6. To circumvent this issue, 12 was converted to the pyridine borane complex (13). Alkylation of 4 with 13 provided 3 after removal of the borane under acidic conditions and saponification of the ester.

MeSH terms

  • Alkylation
  • Boranes / chemistry*
  • Boron Compounds / chemistry*
  • Cyclization
  • Esters / chemistry
  • Hydrogen-Ion Concentration
  • Models, Chemical
  • Pyridines / chemistry*

Substances

  • Boranes
  • Boron Compounds
  • Esters
  • Pyridines
  • pyridine borane
  • pyridine