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Highly efficient chemoselective N-TBS protection of anilines under exceptional mild conditions in the eco-friendly solvent 2-methyltetrahydrofuran†
Andrés R. Alcántara,Wolfgang Holzer
Green Chemistry Pub Date : 07/07/2011 00:00:00 , DOI:10.1039/C1GC15574A
Abstract

A straightforward chemoselective protection of anilines as N-TBS derivatives is described by using a suitable deprotonation of the amine with methyllithium in the environmentally friendly and safer substitute of THF, 2-methyltetrahydrofuran, under exceptional mild reaction conditions (0 °C, 30 min). Interestingly, the protecting group maybe cleaved efficiently by simple treatment of N-TBS-anilines with silica gel in ethanolwater.

Graphical abstract: Highly efficient chemoselective N-TBS protection of anilines under exceptional mild conditions in the eco-friendly solvent 2-methyltetrahydrofuran
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