Hydrochloric Acid → Methyl 5-(3-methoxy-3-oxopropyl)-2,3-dihydrofuro[2,3-c]pyridine-4-carboxylate

温度

150 °C

A mixture of dimethyl 3-hydroxy-5-(3-methoxy-3-oxopropyl)furo[2,3-c]pyridine-2,4-dicarboxylate (3.10 g, 9.19 mmol) and 12M hydrochloric acid (31 mL) was stirred at 150° C. for 1 hr and concentrated under reduced pressure. The residue was dissolved in methanol (60 mL), palladium-carbon powder (600 mg) was added, and the mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure. The residue was dissolved in methanol (60 mL) again, palladium-carbon powder (1.00 g) was added, and the mixture was stirred at 50° C. for 4 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure. The residue was dissolved in methanol (60 mL), 2M trimethylsilyldiazomethane/diethyl ether solution (9.2 mL, 18 mmol) was added under ice-cooling, and the mixture was stirred for 30 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.98 g, yield 81%).

1. concentrationconcentrated under reduced pressure
2. dissolutionThe residue was dissolved in methanol (60 mL)
3. additionpalladium-carbon powder (600 mg) was added
4. stirringthe mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere
5. filtrationThe catalyst was filtered off
6. customthe filtrate was evaporated under reduced pressure
7. dissolutionThe residue was dissolved in methanol (60 mL) again
8. additionpalladium-carbon powder (1.00 g) was added
9. stirringthe mixture was stirred at 50° C. for 4 hr under a hydrogen atmosphere
10. filtrationThe catalyst was filtered off
11. customthe filtrate was evaporated under reduced pressure
12. dissolutionThe residue was dissolved in methanol (60 mL)
13. temperaturecooling
14. stirringthe mixture was stirred for 30 min
15. extractionthe mixture was extracted with ethyl acetate
16. dry with materialThe extract was dried over anhydrous sodium sulfate
17. customthe solvent was evaporated under reduced pressure

ORDレコード

ord-3a6c52ecdc57492ab68a6a362e380d48

出典データセット

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08273761B2