Sodium Iodide → HCID 66662102, compound

HRID 504274Notes

Reaction equation

HRID 504274 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20]([NH:23]C(C)(C)C)(=[O:22])=[O:21])(O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.[I-].[Na+].Cl[Si](C)(C)C>>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[S:20](=[O:22])(=[O:21])[NH:23]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 666616262-(1-benzyl-3-hydroxypyrrolidin-3-yl)-N-(tert-butyl)benzenesulfonamide

Product 1

HCID 66662102HCID 66662102, compoundYield 60.1%

Procedure

To a solution of 2-(1-benzyl-3-hydroxypyrrolidin-3-yl)-N-(tert-butyl)benzene sulfonamide (350 mg, 0.00090 mol) in acetonitrile (15 mL, 0.29 mol) were added sodium iodide (418 mg, 0.00279 mol) and chlorotrimethylsilane (0.354 mL, 0.00279 mol). The reaction mixture was refluxed under nitrogen for 1 hour and then cooled down to room temperature, then quenched with 10% aqueous sodium thiosulfate solution (10 mL), and then extracted with EtOAc. The organic phase was washed with water then brine, and then dried over MgSO4 followed by filtration. The filtrate was concentrated to give the desired compound (170 mg, 60% yield). MS (ESI): 315.0 (M+H+).

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 1 hour
  2. customquenched with 10% aqueous sodium thiosulfate solution (10 mL)
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water
  5. dry with materialbrine, and then dried over MgSO4
  6. filtrationfollowed by filtration
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-82e71633dc42402fb5bc05efabcae658
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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