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

Asit K. Chakraborti; Santosh Rudrawar; Atul Kondaskar

doi:10.1039/B400588K

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Organic & Biomolecular Chemistry

Issue 9, 2004

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

Asit K. Chakraborti , Santosh Rudrawar and Atul Kondaskar

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

DOI: 10.1039/B400588K
Received 13 Jan 2004, Accepted 09 Mar 2004
First published on the web 29 Mar 2004

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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.

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Reactions of various amines with styrene oxide gave a mixture of regioisomers..

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Organic & Biomolecular Chemistry

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

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