Hydrogen Peroxide → (S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Participants

Reaction Steps

To a solution of N-[(2S)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (32 g, 88 mmol, Description 2) in methanol (320 ml) at room temperature under nitrogen, hydrogen peroxide (30 weight % in water, 17.90 ml, 175 mmol) was added and the resulting pale yellow solution stirred overnight. The mixture was then evaporated under reduced pressure and the residue partitioned between EtOAc (500 ml) and water (300 ml). Aqueous phase was back extracted with EtOAc (300 ml) and the combined organics were washed with brine (100 ml)/water (100 ml), dried over Na2SO4 and evaporated to dryness. The resulting pale yellow solid was triturated with Et2O (100 ml)/n-hexane (100 ml) and dried at high vacuum to give N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (20.85 g) as a pale yellow solid.

Provenance & Evidence