Acetic Acid → HCID 58478770, compound

Temperature

15 °C

A suspension of 2-methyl-furo[3,4-b]pyridine-5,7-dione (15 g, 92 mmol) in THF (100 mL) is treated with sodium borohydride (3.75 g, 99 mmol) at 15° C. under an argon atmosphere. The reaction mixture is then treated dropwise with acetic acid (12 g, 200 mmol) at 15° C. During this addition gas evolution is observed. The reaction mixture is stirred at 15° C. for 4 h and is then concentrated. The residue is treated with acetic acid (40 mL) and acetic anhydride (40 mL). The resulting solution is stirred at 100° C. for 3 h. The brown solution is cooled to room temperature and concentrated. The residue is treated with a 20% aqueous NaCl solution and extracted with chloroform. The organic extract is washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated. The residue is purified by chromatography (silica gel, gradient elution, 5:1 hexane/ethyl acetate to 2:1 hexane/ethyl acetate). The product containing fractions are concentrated to give the title compound as a white solid (9.03 g, 44%).

1. additionDuring this addition gas evolution
2. concentrationis then concentrated
3. additionThe residue is treated with acetic acid (40 mL) and acetic anhydride (40 mL)
4. stirringThe resulting solution is stirred at 100° C. for 3 h
5. temperatureThe brown solution is cooled to room temperature
6. concentrationconcentrated
7. additionThe residue is treated with a 20% aqueous NaCl solution
8. extractionextracted with chloroform
9. extractionThe organic extract
10. washis washed with saturated aqueous NaCl solution
11. dry with materialdried over Na2SO4
12. concentrationconcentrated
13. customThe residue is purified by chromatography (silica gel, gradient elution, 5:1 hexane/ethyl acetate to 2:1 hexane/ethyl acetate)
14. additionThe product containing fractions
15. concentrationare concentrated

ORD record

ord-b4214257004947cfa32c101d2497bac7

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977351B2