Acetyl chloride → HCID 59179431, compound

3-(2,3-Dihydrofuro[3,2-c]pyridin-4-yl)propanenitrile (110 mg, 0.63 mmol) and Raney cobalt (200 mg) were suspended in 2M ammonia/ethanol solution (10 mL), and the suspension was stirred at room temperature for 13 hr under a hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was evaporated under reduced pressure. This was dissolved in dichloromethane (5 mL), triethylamine (173 μL, 1.24 mmol) and acetyl chloride (52.8 μL, 0.743 mmol) were added, and the mixture was stirred at room temperature for 20 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate=0/100→10/90) to give the title compound (47 mg, yield 35%).

1. filtrationThe catalyst was filtered through celite
2. customthe filtrate was evaporated under reduced pressure
3. dissolutionThis was dissolved in dichloromethane (5 mL)
4. stirringthe mixture was stirred at room temperature for 20 min
5. extractionthe mixture was extracted with dichloromethane
6. dry with materialThe extract was dried over anhydrous magnesium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customthe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate=0/100→10/90)

ORD record

ord-1d71992ab24a477db76fb4ff5b4a07e5

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273761B2