Tri-<i>tert</i>-butoxychlorosilane (TBOS-Cl) has been shown to be an effective protecting group for various primary amines. The inherent steric bulk of TBOS-Cl allows for mono-protection of primary amines and the potential for further alkylation. Good to moderate yields of protected primary amines were found and purification was simplified as the product is quite non-polar and easily purified in a silica plug with hexanes. Alkylation and deprotection of TBOS-Cl were also investigated.

Bulky silane, tri-<i>tert</i>-butoxychlorosilane, for the protection and alkylation of primary amines

251st National Meeting (2016)

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Bulky silane, tri-tert-butoxychlorosilane, for the protection and alkylation of primary amines