Triethylamine → HCID 67416359, compound

Participants

Reaction Steps

To a solution of crude 1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (55.3 mg, 0.226 mmol, 1 eq) in anhydrous dichloromethane (10 mL) was added isobutyl chloroformate (29.6 μL, 30 mg, 0.226 mmol, 1 eq) and triethylamine (47 μL, 34 mg, 0.338 mmol, 1.5 eq). The mixture was stirred at rt for 4 h. Carbonate resin (3 mmol/g, 150 mg, 0.451 mmol, 2 eq) was added and the reaction is stirred for another 2 h. The mixture was then cooled down to 0° C. and sodium borohydride (25 mg, 0.677 mmol, 3 eq) was added and the mixture stirred at rt for 16 h. After this time, the reaction was filtered, and the filtrate was diluted with dichloromethane then washed with water and brine. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 95:5 dichloromethane/methanol to give 5-hydroxymethyl-1-(4-methoxy-benzyl)-1H-pyridin-2-one. Mass Spec m/z=232 [M+H+].

Provenance & Evidence