HCID 58636705, compound → HCID 58636730, compound

Participants

Reaction Steps

To a solution of 5-(3-cyano-benzyloxy)-4-formyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (109) (1.4 g, 2.9 mmol) in anhydrous tetrahydrofuran (50 mL) was slowly added methyl magnesium bromide (4 mL, 1.0 M, 4.0 mmol) at −78° C. under nitrogen atmosphere and stirred for 30 minutes. The reaction mixture was quenched with a solution of saturated aqueous sodium bicarbonate, and the crude product extracted with ethyl acetate and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using a gradient mixture of ethyl acetate:hexane (0:1 to 3:2) as an eluant to give [5-(3-cyano-benzyloxy)-4-(1-hydroxy-ethyl)-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (112) (1.04 g, 72% yield).

Provenance & Evidence