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

HRID 473117Notes

Reaction equation

HRID 473117 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][C@@H:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]3)O1.CC(C)=[O:28]>O>[OH:28][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][C@@H:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]2

Participants

4

Reactant 2

HCID 180AcetoneHCID 68155795(R)-N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 68156499(R)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamideYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of (R)-N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (6.21 mmol, 2.27 g) in acetone (20.00 mL), a solution of oxone monopersulfate compound (6.84 mmol, 4.20 g) in Water (20 mL) was added dropwise over 2 min. The resultant solution was stirred for a further 10 min before being quenched with NaHSO3 (aq). The solution was extracted with DCM (×3), dried (MgSO4), filtered and concentrated in vacuo to give the crude product as a colourless oil which solidified to a white solid on standing. The solid was triturated with heptane to give the title compound as a white solid (1.46 g, 92%). MS (ESI): m/z [M−H]− 254.0

Workup

  1. custombefore being quenched with NaHSO3 (aq)
  2. extractionThe solution was extracted with DCM (×3)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product as a colourless oil which
  7. customThe solid was triturated with heptane

Sources & evidence

ORD record
ord-927345521868493da182d90ecb4907d5
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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