Diisopropylamine → 3-(1-Methylcyclopropyl)-3-oxopropanenitrile

Temperature

-78 °C

To a solution of diisopropylamine (7.43 ml, 52.6 mmol) in 60 mL of THF at −78° C. was added a solution of n-BuLi in hexanes (2.5M, 21.0 mL, 52.6 mmol). The mixture was stirred at −78° C. for 30 min then acetononitrile (2.76 ml, 52.6 mmol) was added. After 30 min, methyl 1-methylcyclopropanecarboxylate (3.0 g, 52.6 mmol) was added and the reaction mixture was stirred at −78° C. for 1 hour then allowed to warm to room temperature and stirred overnight. The mixture was concentrated and the residue was diluted with water and extracted with ether. The aqueous phase was acidified with 6N aqueous HCl to pH 2-3 and extracted with ether. The combined organic extracts were dried over MgSO4, filtered, and concentrated to afford the title compound 2.89 g (89%). MS (DCI/NH3) m/z 124 (M+H)+.

1. additionwas added
2. waitAfter 30 min
3. stirringthe reaction mixture was stirred at −78° C. for 1 hour
4. temperatureto warm to room temperature
5. stirringstirred overnight
6. concentrationThe mixture was concentrated
7. additionthe residue was diluted with water
8. extractionextracted with ether
9. extractionextracted with ether
10. dry with materialThe combined organic extracts were dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-b8defc9de93b498b93b20d4c33ea05b0

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859596B2