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N-Urethane protection of amines and amino acids in an ionic liquid†
M. L. Di Gioia,A. Gagliardi,A. Leggio,V. Leotta,E. Romio,A. Liguori
RSC Advances Pub Date : 07/20/2015 00:00:00 , DOI:10.1039/C5RA12121C
Abstract

An efficient, solvent-free protocol for the N-fluorenylmethoxycarbonylation and N-benzyloxycarbonylation of amines is described. The reaction of aliphatic and aromatic amines with FmocOSu and Cbz-Osu in [Bmim][BF4] at room temperature afforded the corresponding N-urethane derivatives in excellent yields and do not require any further purification. The method has been extended to the N-Fmoc and N-Cbz protection of amino acids. Absence of bases, very short reaction times, high yields, selectivity and ease of product separation are some advantages of this protocol.

Graphical abstract: N-Urethane protection of amines and amino acids in an ionic liquid
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