Tetrahedron letters

Selective nitrogen protection of hydroxyalkylbenzimidazoles using 2, 2, 2-trichloroethylchloroformate

RC Woudenberg, EB Coughlin

Index: Woudenberg, Richard C.; Coughlin, E. Bryan Tetrahedron Letters, 2005 , vol. 46, # 37 p. 6311 - 6313

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Citation Number: 4

Abstract

A method for selective N-protection of hydroxyalkylbenzimidazoles using 2, 2, 2- trichloroethylchloroformate (Troc-Cl) applicable to various alkyl chain lengths has been developed. In the specific case of 5-(1-[2, 2, 2-trichloroethyl formyl]-benzimidazol-2-yl)- propan-1-ol, migration of Troc from the benzimidazole to the primary alcohol occurs in the presence of triethylamine, allowing the choice of selective N-Troc or O-Troc protection.