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 was added n-BuLi (2.5M) (21.03 mL, 52.6 mmol) at −78° C. The reaction was stirred at −78° C. for 30 min, then acetononitrile (2.76 mL, 52.6 mmol) was added at −78° C. and the reaction was stirred for 30 min, then methyl 1-methylcyclopropanecarboxylate (3 g, 52.6 mmol) was added at −78° C. The reaction was stirred at −78° C. for 1 hour and then allowed to warm up at room temperature overnight. The solvent was evaporated and the solid dissolved in water. The aqueous layer was washed with ether and then acidified with 6N HCl to pH 2-3. The aqueous layer was extracted with ether. The organic layer was dried with MgSO4 and concentrated to afford the title compound (2.89 g, 89%). MS (DCI/NH3) m/z 124 (M+H)+.

1. additionwas added at −78° C.
2. stirringthe reaction was stirred for 30 min
3. stirringThe reaction was stirred at −78° C. for 1 hour
4. temperatureto warm up at room temperature overnight
5. customThe solvent was evaporated
6. dissolutionthe solid dissolved in water
7. washThe aqueous layer was washed with ether
8. extractionThe aqueous layer was extracted with ether
9. dry with materialThe organic layer was dried with MgSO4
10. concentrationconcentrated

ORD record

ord-baff84edc84347e5a18b166f9ed6785a

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08492371B2