Diethyl Ether → HCID 86659447, compound

Temperature

-78 °C

In a flask, isobutyronitrile (6.39 g, 92.4 mmol) was dissolved in diethyl ether (190 mL) and cooled at −78° C. NaHMDS (1.0 M in THF, 99.0 mL, 99.0 mmol) was added and the mixture stirred for 30 min at −78° C. A solution of (R)-2-methyl-propane-2-sulfinic acid (E)-ethylideneamide (crude from step 1, 5.21 g, 33.0 mmol) in THF (50.0 mL) was slowly added. The mixture was stirred at −78° C. for 2 h then allowed to warm to room temperature overnight. The reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4 and concentrated. The residue was purified by SiO2 chromatography (20-100% EtOAc/hexane) to afford 2.93 g (41%) (R)-2-methyl-propane-2-sulfinic acid ((S)-2-cyano-1,2,2-trimethyl-ethyl)-amide as a light yellow oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 3.28 (dq, J=8.7, 6.4 Hz, 1H), 3.08 (d, J=8.7 Hz, 1H), 1.45 (d, J=6.4 Hz, 3H), 1.39 (s, 3H), 1.34 (s, 3H), 1.26 (s, 9H).

1. stirringThe mixture was stirred at −78° C. for 2 h
2. temperatureto warm to room temperature overnight
3. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
4. extractionextracted with EtOAc
5. washThe combined organics were washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe residue was purified by SiO2 chromatography (20-100% EtOAc/hexane)

ORD record

ord-95395137e8e64e61bbf2596b172d9452

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2