Ammonium Chloride → HCID 117759619, compound

Temperature

-78 °C

Under a nitrogen atmosphere, a solution (1.8 M, 5.29 mL) of trimethylaluminum in toluene was added to a solution of 3-(3-(3-((methoxymethoxy)methyl)phenyl)oxiran-2-yl)propanenitrile (1.07 g) in THF (50 mL) at −78° C., and the mixture was stirred at −78° C. for 20 min. To the reaction mixture was added dropwise a solution (1.0 M, 6.49 mL) of lithium hexamethyldisilazane in THF at −78° C., and the mixture was stirred at −78° C. for 30 min. The reaction mixture was stirred at room temperature for 10 min, saturated aqueous ammonium chloride solution was added at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (457 mg, less polar) as a pale-yellow oil and a stereoisomer (345.5 mg, more polar) of the title compound as a pale-yellow oil.

1. stirringthe mixture was stirred at −78° C. for 30 min
2. stirringThe reaction mixture was stirred at room temperature for 10 min
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-4be0d2a37957402891bfef9c7f2f4105

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382188B2