Acetic Acid → HCID 58636780, compound

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Reaction Steps

A mixture of [5-(3-cyano-benzyloxy)-6-formyl-4-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (141) (140 mg, 0.3 mmol), sodium cyanide (272 mg, 5.5 mmol), manganese (IV) dioxide (422 mg, 85%, 0.29 mmol), acetic acid (256 mg, 4.2 mmol) in methyl alcohol (40 mL) was stirred at room temperature for 12 hours. The solid was filtered through a celite pad and washed several times with methanol. The filtrate was evaporated to give a crude residue, which was purified by column chromatography on silica gel using a gradient mixture of ethyl acetate:hexane (0:1 to 1:0) as eluant to give 5-{[tert-butoxycarbonyl-(4-cyano-phenyl)-amino]-methyl}-3-(3-cyano-benzyloxy)-4-methyl-pyridine-2-carboxylic acid methyl ester (143) (142 mg, 96% yield) as a light yellow oil.

Provenance & Evidence