An efficient synthesis of 2-amino alcohols by silica gel catalysed opening of epoxide rings by amines.
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.
Chakraborti
Asit K
AK
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar 160 062, Punjab, India. akchakraborti@niper.ac.in
Rudrawar
Santosh
S
Kondaskar
Atul
A
D000588:Amines / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D000605:Amino Alcohols; D004852:Epoxy Compounds; D058428:Silica Gel; D012822:Silicon Dioxide