Sodium Thiosulfate → 1-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(methylsulfonyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

HRID 1411288Notes

Reaction equation

HRID 1411288 reaction equation
CS[C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])[C:6]2=[CH:7][CH:8]=1.Cl[C:33]1C=CC=C(C(OO)=O)C=1.[S:43]([O-:47])([O-])(=[O:45])=S.[Na+].[Na+]>C(Cl)Cl>[CH3:33][S:43]([C:3]1[CH:4]=[C:5]2[C:11]3([CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[CH2:10][N:9]([C:23]([O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:29])[CH3:30])=[O:24])[C:6]2=[CH:7][CH:8]=1)(=[O:47])=[O:45]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 904498511-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(methylthio)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

Product 1

HCID 904496081-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(methylsulfonyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-(Trimethylsilyl)ethyl) 1′-tert-butyl 5-(methylthio)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (192 mg, 0.41 mmol) was dissolved in methylene chloride (5 mL). Thereafter, meta-chloroperbenzoic acid (350 mg, 2.03 mmol) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred for 30 minutes. Thereafter, an aqueous solution of sodium thiosulfate was added to the reaction solution, and the mixed solution was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(methylsulfonyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (133.2 mg, 65%) in the form of a white amorphous product.

Workup

  1. temperatureunder cooling on ice
  2. extractionthe mixed solution was then extracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration in vacuo
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4675da5be3a24178a4f3612aae698966
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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