
%0 Journal Article
%A Indusegaram, Sutharsiny 
%A Katsifis, Andrew G. 
%A Ridley, Damon D. 
%A Vonwiller, Simone C. 
%T Nitrogen versus Oxygen Group Protection in Hydroxypropylbenzimidazoles
%J Australian Journal of Chemistry
%D 2003/07/18
%V 56
%N 8
%P 819-827
%K 
%R https://doi.org/10.1071/CH03012
%U https://www.publish.csiro.au/paper/CH03012 
%X In order to convert 1&#8242;H-benzimidazol-2&#8242;-ylpropanols into aryl ethers using Mitsunobu coupling, it was necessary to protect the benzimidazole nitrogen in the starting alcohols. Selective protection at nitrogen was achieved through N-benzyl derivatives, but attempts to protect the nitrogen directly through tert-butoxycarbonyl, acetyl, trityl, or tetrahydropyranyl derivatives were complicated either by selective reactions at oxygen or by the formation of bis-protected compounds. Transformations of some oxygen-protected derivatives are discussed, and in particular the conversion of the acetates of 1&#8242;H-benzimidazol-2&#8242;-ylpropanols to N-tetrahydropyranyl derivatives is described. Mitsunobu coupling involving the N-benzyl and N-tetrahydropyranyl derivatives and methyl 4-hydroxybenzoate were achieved, and thus afforded synthetic routes to the desired propylbenzimidazole aryl ethers. 
