
TY  - JOUR
A1  - Indusegaram, Sutharsiny 
A1  - Katsifis, Andrew G. 
A1  - Ridley, Damon D. 
A1  - Vonwiller, Simone C. 
T1  - Nitrogen versus Oxygen Group Protection in Hydroxypropylbenzimidazoles
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2003
VL  - 56
IS  - 8
SP  - 819
EP  - 827
KW  - 
UR  - https://doi.org/10.1071/CH03012 
N2  - 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. 
ER  -

