Isobutyronitrile → 2-Methylpropane-2-sulfinic acid (2-cyano-1-cyclopropyl-2,2-dimethyl-ethyl)-amide

Temperature

-78 °C

To a solution of isobutyronitrile (0.30 g, 4.35 mmol) in THF (8 mL) at −78° C. was added LiHMDS (1.0M in THF, 4.8 mL, 4.8 mmol). The pale yellow reaction mixture was stirred at −78° C. for 30 min then a solution of 2-methyl-propane-2-sulfinic acid 1-cyclopropyl-meth-(E)-ylideneamide (0.50 g, 2.90 mmol) [prepared according to WO2008/147800] in THF (2 mL) was slowly added. The reaction mixture was stirred at −78° C. for 2 h then quenched with saturated aqueous NH4Cl and warmed to room temperature. The mixture was diluted with water and extracted with EtOAc (2×). The combined organics were dried over MgSO4 and concentrated to afford 0.70 g of 2-methylpropane-2-sulfinic acid (2-cyano-1-cyclopropyl-2,2-dimethyl-ethyl)-amide as a viscous colorless oil.

1. stirringThe reaction mixture was stirred at −78° C. for 2 h
2. customthen quenched with saturated aqueous NH4Cl
3. temperaturewarmed to room temperature
4. additionThe mixture was diluted with water
5. extractionextracted with EtOAc (2×)
6. dry with materialThe combined organics were dried over MgSO4
7. concentrationconcentrated

ORD record

ord-106c3b78188242f2b93129c026aec0dd

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481541B2