HCID 86732205, compound → HCID 86732204, compound

Participants

Reaction Steps

Ru[p-cymeme](1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (0.119 g, 0.198 mmol) was added in one portion to a solution of (R)-N-((S)-2-(3-bromophenyl)-1,5,5,5-tetrafluoro-4-oxopentan-2-yl)-2-methylpropane-2-sulfinamide (2.14 g, 4.95 mmol) in IPA (50 ml) (which had been degassed by bubbling nitrogen through the solution for 30 minutes prior to use) in a dry box at room temperature. After stirring overnight, the reaction was worked up with saturated sodium bicarbonate solution and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography using 20-100% EtOAc/hexane to give (R)-N-((2S,4S)-2-(3-bromophenyl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (1.83 g, 85% yield). MS m/z=435.8 [M+H]+. Calculated for C15H20BrF4NO2S: 434.3

Provenance & Evidence