Water → (R)-2-methyl-propane-2-sulfinic acid [(S)-1-(4-bromo-2-methyl-phenyl)-ethyl]amide

Lithium tri-sec-butylborohydride (1 mol/L in tetrahydrofuran, 59.2 mL) was added to a solution of (R)-2-methyl-propane-2-sulfinic acid [1-(4-bromo-2-methyl-phenyl)-ethylidene]-amide (6.24 g) in tetrahydrofuran (50 mL) chilled in an ice bath. The solution was stirred for 2 h while warming to room temperature in the cooling bath. The solution was then cooled again in an ice bath prior to the careful addition of water. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with water, saturated aqueous NaHCO3 solution, and brine. After drying (MgSO4) and evaporating the solvent, the title compound was obtained that was directly submitted to the next reaction step. Yield: 8.85 g (ca. 75% pure); Mass spectrum (ESI−): m/z=318/320 (Br) [M+H]+.

1. temperaturechilled in an ice bath
2. temperatureThe solution was then cooled again in an ice bath
3. extractionThe resulting mixture was extracted with ethyl acetate
4. washthe combined extracts were washed with water, saturated aqueous NaHCO3 solution, and brine
5. dry with materialAfter drying (MgSO4)
6. customevaporating the solvent

ORD record

ord-40f6a8850e04412bb27845ebd3a9e246

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680093B2