Water → HCID 90449233, compound

HRID 1411271Notes

Reaction equation

HRID 1411271 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([S:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[CH:15]=3)[N:10](C(=O)C(F)(F)F)[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[OH:30].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[OH2:45]>C(Cl)Cl>[CH:18]1([S:17]([C:14]2[CH:15]=[C:16]3[C:6]4([CH2:7][CH2:8][N:4]([C:1](=[O:3])[CH3:2])[CH2:5]4)[CH2:9][NH:10][C:11]3=[CH:12][CH:13]=2)(=[O:30])=[O:45])[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 90449363HCID 90449363, compound

Product 1

HCID 90449233HCID 90449233, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1′-Acetyl-5-(cyclopentylthio)spiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (13 mg, 0.032 mmol) was dissolved in methylene chloride (1 mL). Thereafter, sodium hydrogen carbonate (8 mg, 0.096 mmol) was added to the above obtained solution, and then, under cooling on ice, m-chloroperbenzoic acid (11 mg, 0.064 mmol) was further added thereto. The thus obtained mixture was stirred at room temperature for 1 hour. Thereafter, the reaction solution was diluted with water, and was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water, and brine, and was then dried over anhydrous magnesium sulfate, followed by concentration in vacuo. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1). The obtained colorless oily product was dissolved in methanol (1 mL). A saturated solution of ammonium-methanol (0.5 mL) was added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 15 minutes. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by preparative thin-layer chromatography (chloroform:methanol=10:1) to obtain 1-(5-(cyclopentylsulfonyl)spiro[indoline-3,3′-pyrrolidin]-1′-yl)ethanone (2 mg, 17%) in the form of a colorless oily product.

Workup

  1. additionwas further added
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water, and brine
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. concentrationfollowed by concentration in vacuo
  6. customThe obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1)
  7. dissolutionThe obtained colorless oily product was dissolved in methanol (1 mL)
  8. additionA saturated solution of ammonium-methanol (0.5 mL) was added to the above obtained solution
  9. stirringthe thus obtained mixture was then stirred at room temperature for 15 minutes
  10. concentrationThereafter, the reaction solution was concentrated in vacuo
  11. customthe obtained residue was then purified by preparative thin-layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-02d86074e6d046fcb111a86b11c8f5a0
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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