Sodium Bicarbonate → HCID 58636750, compound

Participants

Reaction Steps

To a solution of [5-(3-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (106) (51.1 g, 0.10 mol) in dry dichloromethane (700 mL) was slowly added bis(2-methoxyethyl)aminosulfur trifluoride (39.7 g, 0.18 mol) at 0° C. under nitrogen atmosphere. The reaction was slowly warmed to room temperature and stirred for 2 hours. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product extracted with dichloromethane, 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 dichloromethane:acetone (1:0 to 18:1) as an eluant to give [5-(3-cyano-benzyloxy)-4-fluoromethyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (107) (41.3 g, 80% yield) as a colorless solid.

Provenance & Evidence