A. Schweifer, I. Zolle, F. Wuggenig
Apr 17, 2010
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Journal
Monatshefte für Chemie - Chemical Monthly
Abstract
Ethyl 2,2′-bipyridine-5-carboxylate was converted to (2,2′-bipyridine-5-yl)methanol and (S)-1-(2,2′-bipyridine-5-yl)ethanol. The latter synthesis comprised five steps and resolution by HPLC on a chiral stationary phase. Both alcohols were reacted with methyl 1H-imidazole-5-carboxylate in a Mitsunobu reaction to give mixtures of the desired methyl 1-(2,2′-bipyridine-5-yl)alkyl-1H-imidazole-5-carboxylate as main product and the methyl 1-(2,2′-bipyridine-5-yl)alkyl-1H-imidazole-4-carboxylate as side product. The structure of (R)-(−)-methyl 1-(2,2′-bipyridine-5-yl)ethyl-1H-imidazole-4-carboxylate was determined by X-ray structure analysis.Graphical abstract