Potassium hydroxy sulfite → N-(5-hydroxy-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

HRID 473089Notes

Reaction equation

HRID 473089 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH:14]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:13][CH2:12]3)O1.[OH:26]OS([O-])=O.[K+]>CC(C)=O.O>[OH:26][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:13][CH2:12]2

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 66733919N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

Product 1

HCID 70223457N-(5-hydroxy-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamideYield 100.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (1.5 g, 4.11 mmol) in acetone (15 mL) was added dropwise a solution of oxone (2.78 g, 4.52 mmol) in water (15 mL). The resulting mixture stirred for another 10 min before the reaction mixture quenched with Na2O5S2 solution and diluted with DCM. The organic layer was separated, washed with brine (2×) and dried on Na2SO4. Solvent evaporated in vacuo to afford the title compound as a white solid (1.05 g, 100%). MS (ESI): m/z [M−H]− 254.0

Workup

  1. customquenched with Na2O5S2 solution
  2. additiondiluted with DCM
  3. customThe organic layer was separated
  4. washwashed with brine (2×)
  5. customdried on Na2SO4
  6. customSolvent evaporated in vacuo

Sources & evidence

ORD record
ord-4a95a76f3617488f87da2524f5689cca
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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