Diisobutylaluminum hydride → HCID 117833499, compound

Participants

Reaction Conditions

Reaction Steps

Intermediate XVI-1: In a dry flask under an inert atmosphere the light yellow solution of (S)-ethyl 3-((S)-1,1-dimethylethylsulfinamido)-4,4-difluoro-3-(2-fluorophenyl)butanoate (XV-2) (2.59 g, 7.09 mmol) in DCM (75 ml) was treated dropwise with DIBAH (1 M in toluene; 10.6 ml, 10.6 mmol) keeping the internal temperature below −72° C. After complete addition the reaction mixture was stirred at −78° C. for 30 min. For the workup, the mixture was quenched with a saturated solution of NH4Cl (10 ml), left to warm to room temperature and stirred for 30 min. The thick suspension was filtered through a layer of Dicalite® which was washed twice with DCM. The filtrate was treated with a half-saturated solution of NH4Cl and extracted three times with DCM. The combined organic layers were dried over MgSO4 and evaporated. The crude product was purified by chromatography on silica gel (eluent: heptane/AcOEt; gradient: 30-50% AcOEt) to yield the (S)—N—((S)-1,1-difluoro-2-(2-fluorophenyl)-4-oxobutan-2-yl)-2-methylpropane-2-sulfinamide (XVI-1) (704 mg, 31% yield) as a light yellow oil and the starting ester XV-2 (1.28 g, 49% yield) as a colorless oil. MS: m/z=322.4 (M+H)+.

Provenance & Evidence