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Issue 9, 2013
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A waste-minimized protocol for the preparation of 1,2-azido alcohols and 1,2-amino alcohols

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Abstract

Under solvent-free conditions the reaction of epoxides 1a–i with trimethylsilylazide (2) catalyzed by polystiryl-supported fluoride (PS-DABCOF2) has led to the efficient preparation of the corresponding O-TMS protected 1,2-azido alcohols 3a–i that, by treatment with Dowex-H, gave the related 1,2-azido alcohols 4a–i in excellent yields (83–99% and 82–96%, respectively). The use of a flow procedure has allowed us to significantly minimize waste in the preparation of representative 1,2-azido alcohols 4a, 4c and 4i that have been obtained with E-factors of 1.6, 2.1, and 1.9, respectively. The 1,2-amino alcohols 5a, 5c and 5f have been also prepared, in quantitative yields, by reduction of the corresponding O-TMS protected 1,2-azido alcohols 3a, 3c, and 3f by Pd on the Al2O3/HCOOH system.

Graphical abstract: A waste-minimized protocol for the preparation of 1,2-azido alcohols and 1,2-amino alcohols

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Article information


Submitted
30 May 2013
Accepted
21 Jun 2013
First published
21 Jun 2013

Green Chem., 2013,15, 2394-2400
Article type
Paper

A waste-minimized protocol for the preparation of 1,2-azido alcohols and 1,2-amino alcohols

E. Ballerini, P. Crotti, I. Frau, D. Lanari, F. Pizzo and L. Vaccaro, Green Chem., 2013, 15, 2394
DOI: 10.1039/C3GC40988K

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