Sodium Iodide → HCID 66662102, compound

HRID 2275528Notes

Reaction equation

HRID 2275528 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 filteration. 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. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2b57abb18a4b489384f43e3c9def6558
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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