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

HRID 473080Notes

Reaction equation

HRID 473080 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.[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)[CH2:14][C@H:13]([NH:18][S:19]([CH:22]([CH3:24])[CH3:23])(=[O:21])=[O:20])[CH2:12]2

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 46899977(S)-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 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of (S)-N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide (6.95 mmol, 2.54 g) in Acetone (20.00 mL), a solution of Oxone(R), monopersulfate compound (7.65 mmol, 4.70 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 pale yellow oil (2.42 g). On standing the reaction mixture solidified to a pale yellow solid in an oily residue. The solid was triturated with heptane then ether to give the title compound as an off white solid (1.66 g, 94%). 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 pale yellow oil (2.42 g)
  7. customThe solid was triturated with heptane

Sources & evidence

ORD record
ord-ad4aeca247074ec29a1ad859c3e54e12
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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