Mechanochemical deprotection of t-butoxycarbonyl (Boc) group using basic alumina†

Abstract

A solvent-free, operationally simple, and chemoselective mechanochemical method for t-butoxycarbonyl (Boc) deprotection is described. In a planetary ball mill, N-Boc groups from protected heterocycles, amides, and anilines, as well as O-Boc groups from carbonates, can be removed selectively, using basic alumina. This high-yielding protocol avoids tedious extraction and column chromatography.