Potassium Carbonate → HCID 178517420, compound

Temperature

80 °C

A solution of trimethylaluminum in toluene (2M, 25 mL, 50 mmol) was added slowly under nitrogen to a suspension of ammonium chloride (2.9 g, 54 mmol) in anhydrous toluene at 0° C.-5° C. The mixture was then stirred at a temperature in the range of 15° C. to 40° C. for 20 min before addition of a solution of cyclopentanecarbonitrile (3.13 mL, 30 mmol) in toluene. The resulting mixture was then heated at 80° C. under stirring for 10 hours. Thereafter, the mixture was cooled to a temperature in the range of 15° C. to 40° C. MeOH was slowly added to quench the reaction and stirred at a temperature in the range of 15° C. to 40° C. for 1 hour. Thereafter, the precipitate was filtered and washed with MeOH (3×30 mL). The filtrate and the washings were combined and concentrated under reduced pressure. After drying under vacuum, the crude solid (3.5 g) was dissolved in anhydrous EtOH (20 mL). Methyl-2-oxo-cyclopentanecarboxylate (3.1 mL, 25 mmol) and K2CO3 (4.14 g, 30 mmol) were added sequentially to this solution and the mixture was heated to reflux for a period over 6-15 hours. Thereafter, volatiles were evaporated under reduced pressure and the mixture was diluted with ice-water under stirring. The resultant precipitate was filtered, washed thoroughly with water followed by ether and dried under vacuum (4.6 g, 95.4% yield).

1. temperatureThereafter, the mixture was cooled to a temperature in the range of 15° C. to 40° C
2. customto quench
3. customthe reaction
4. stirringstirred at a temperature in the range of 15° C. to 40° C. for 1 hour
5. filtrationThereafter, the precipitate was filtered
6. washwashed with MeOH (3×30 mL)
7. concentrationconcentrated under reduced pressure
8. customAfter drying under vacuum
9. dissolutionthe crude solid (3.5 g) was dissolved in anhydrous EtOH (20 mL)
10. temperaturethe mixture was heated
11. temperatureto reflux for a period over 6-15 hours
12. customThereafter, volatiles were evaporated under reduced pressure
13. additionthe mixture was diluted with ice-water
14. stirringunder stirring
15. filtrationThe resultant precipitate was filtered
16. washwashed thoroughly with water
17. customdried under vacuum (4.6 g, 95.4% yield)

ORD record

ord-65d5b4dec66d42e7a7a7e311e59a8d17

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989463B2