Triacetoxyperiodinane → HCID 58636705, compound

Participants

Reaction Steps

A mixture of Dess-Martin periodinone (5.0 g, 11.8 mmol) and [5-(3-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (106) (5.26 g, 10.8 mmol) in dichloromethane (200 mL) was stirred at room temperature for 30 minutes. The reaction mixture was then poured into a 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 ethyl acetate:hexane (0:1 to 2:3) as an eluant to give [5-(3-cyano-benzyloxy)-4-formyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (109) (4.6 g, 88% yield) as a colorless solid.

Provenance & Evidence