Triacetoxyperiodinane → HCID 86732114, compound

Participants

Reaction Steps

A 100 mL flask containing (R)-N-((S)-2-(5-Bromo-2-fluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide (4c, 2.472 g, 6.75 mmol) under nitrogen was placed in a water bath and treated with Dess-Martin periodinane (Aldrich; 0.3 M in CH2Cl2; 25 mL, 7.50 mmol). The mixture was stirred at ambient temperature for 3 h, after which the reaction was quenched with saturated aqueous sodium thiosulfate solution (7.5 mL) and stirred for 15 min. The product was extracted into CH2Cl2 from saturated aqueous NaHCO3, dried over Na2SO4, concentrated, and purified by chromatography on silica gel [Gradient: 20%→100% EtOAc/hexane] to give (R)-N-((S)-2-(5-bromo-2-fluorophenyl)-4-oxobutan-2-yl)-2-methylpropane-2-sulfinamide (2.03 g, 5.57 mmol) as a colorless gum. MS m/z=365.9 [M+H]+. Calculated for C14H19BrFNO2S: 364.3

Provenance & Evidence