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

*Department of Medicinal Chemistry, National Insitute of Pharmaceutical Education and Research, Sector 67, S. A. S. Nagar 160 062, Punjab, India, Email: akchakrabortiniper.ac.in

A. K. Chakraborti, S. Rudrawar, A. Kondaskar, Org. Biomol. Chem., 2004, 2, 1277-1280.

DOI: 10.1039/b400588k

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Abstract

Silica gel (60–120 mesh) efficiently catalyses the opening of epoxides by amines at r.t. under solvent-free conditions. Non-styrenoidal unsymmetrical alkene oxides undergo selective nucleophilic attack at the sterically less hindered carbon by aniline. A complementary regioselectivity is exhibited by aromatic and aliphatic amines during the reaction with styrene oxide.

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Zinc(II) Perchlorate Hexahydrate Catalyzed Opening of Epoxide Ring by Amines: Applications to Synthesis of (RS)/(R)-Propranolols and (RS)/(R)/(S)-Naftopidils

Shivani, B. Pujala, A. K. Chakraborti, J. Org. Chem., 2007, 72, 3713-3722.

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Key Words

Epoxides, 1,2-Amino Alcohols

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ID: J52-Y2004-220