Issue 9, 2004
From the journal:

Organic & Biomolecular Chemistry

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

Asit K. Chakraborti,*a   Santosh Rudrawara  and  Atul Kondaskara  

* Corresponding authors

a Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar 160 062, Punjab, India
E-mail: akchakraborti@niper.ac.in

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.

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

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Article information

DOI
https://doi.org/10.1039/B400588K
Article type
Paper
Submitted
13 Jan 2004
Accepted
09 Mar 2004
First published
29 Mar 2004

Org. Biomol. Chem., 2004,2, 1277-1280

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

A. K. Chakraborti, S. Rudrawar and A. Kondaskar, Org. Biomol. Chem., 2004, 2, 1277 DOI: 10.1039/B400588K

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