Triethylamine → HCID 67416359, compound

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+].

1. stirringthe reaction is stirred for another 2 h
2. temperatureThe mixture was then cooled down to 0° C.
3. stirringthe mixture stirred at rt for 16 h
4. filtrationAfter this time, the reaction was filtered
5. additionthe filtrate was diluted with dichloromethane
6. washthen washed with water and brine
7. dry with materialThe organic layer was dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by column chromatography
11. washeluting with 95:5 dichloromethane/methanol

ORD record

ord-8bdd26cf0b6f49e09b3aad947335a64e

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791147B2