Sodium borohydride → [3,3']bipyridinyl-5-yl-methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of [3,3′]bipyridinyl-5-carboxylic acid ethyl ester (1 eq) in ethanol was added sodium borohydride (2 eq) at room temperature. The reaction mixture was heated in a 50° C. oil bath for 60 minutes and then quenched by addition of H2O. Once the reaction solvent was removed in vacuo, a solution of the residue in dichloromethane was washed with NaCl(sat), dried over sodium sulfate, filtered and concentrated. The crude solid was purified by flash chromatography using a solvent gradient of 95% DCM, 5% MeOH and 0.1% TEA to yield [3,3′]bipyridinyl-5-yl-methanol (34%). MH+(187).

Provenance & Evidence