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 h and then allowed to warm up at rt 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 h
4. temperatureto warm up at rt 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-1412730b1bc745959c8e89b44497a969

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193713B2