Tetrahydrofuran → HCID 67235388, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-ethyl 3-(5-bromo-2-fluorophenyl)-3-((R)-1,1-dimethylethylsulfinamido)-2,2-difluorobutanoate (intermediate A3C) (10.5 g, 23.6 mmol) in anhydrous THF (150 ml) at −78° C. was dropwise added a methylmagnesium bromide solution (3.2 M in 2-methyl-THF; 59.1 ml, 189 mmol), the cooling bath was removed and the mixture was stirred at 23° C. for 18 h. Poured cautiously into sat. NH4Cl-sol., extracted with ethyl acetate, washed organic layer with brine and dried over Na2SO4. Removal of the solvent in vacuum left the (R)-N-((R)-2-(5-bromo-2-fluorophenyl)-3,3-difluoro-4-hydroxy-4-methylpentan-2-yl)-2-methylpropane-2-sulfinamide (10.565 g, 23.6 mmol, 99.7% yield) as a yellow gum, which was used in the next step without further purification. MS (ISP): m/z=430.1 [(M+H)+] and 432.1 [(M+2+H)+].

Provenance & Evidence