Issue 9, 2013
From the journal:

Green Chemistry

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

Eleonora Ballerini,a   Paolo Crotti,b   Ileana Frau,b   Daniela Lanari,c   Ferdinando Pizzoa  and  Luigi Vaccaro*a  

* Corresponding authors

a Laboratory of Green Synthetic Organic Chemistry, CEMIN – Dipartimento di Chimica, Università di Perugia Via Elce di Sotto, 8, Perugia, Italia
E-mail: luigi@unipg.it
Fax: +39 075 5855560
Tel: +39 075 5855541

b Dipartimento di Farmacia, Università di Pisa, Via Bonanno 33, Pisa, Italy

c Dipartimento di Chimica e Tecnologia del Farmaco, Università di Perugia, Via del Liceo, Italy

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

DOI
https://doi.org/10.1039/C3GC40988K
Article type
Paper
Submitted
30 May 2013
Accepted
21 Jun 2013
First published
21 Jun 2013

Green Chem., 2013,15, 2394-2400

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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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