An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines

Org Biomol Chem. 2004 May 7;2(9):1277-80. doi: 10.1039/b400588k. Epub 2004 Mar 29.

Abstract

Silica gel (60-120 mesh) efficiently catalyses the opening of epoxide rings by amines at rt under solvent-free conditions providing an easy method for the synthesis of 2-amino alcohols. Aromatic and aliphatic amines react with cyclohexene oxide with exclusive formation of the trans-2-aryl/alkylaminocyclohexanols in high yields. A complementary regioselectivity is exhibited by aromatic and aliphatic amines during the reaction with styrene oxide. The epoxide ring of non-styrenoidal unsymmetrical alkene oxide undergoes selective nucleophilic attack at the sterically less hindered carbon by aniline.

MeSH terms

  • Amines / chemistry*
  • Amino Alcohols / chemical synthesis*
  • Catalysis
  • Epoxy Compounds / chemistry*
  • Molecular Structure
  • Silica Gel
  • Silicon Dioxide / chemistry*
  • Stereoisomerism

Substances

  • Amines
  • Amino Alcohols
  • Epoxy Compounds
  • Silica Gel
  • Silicon Dioxide