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

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.

1. customThe mixture was then evaporated under reduced pressure
2. customthe residue partitioned between EtOAc (500 ml) and water (300 ml)
3. extractionAqueous phase was back extracted with EtOAc (300 ml)
4. washthe combined organics were washed with brine (100 ml)/water (100 ml)
5. dry with materialdried over Na2SO4
6. customevaporated to dryness
7. customThe resulting pale yellow solid was triturated with Et2O (100 ml)/n-hexane (100 ml)
8. customdried at high vacuum

ORD record

ord-179bd276a16f4a7f924f207917a7dcf6

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173820B2