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

HRID 1411288
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1411288
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]
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Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4675da5be3a24178a4f3612aae698966
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08921576B2

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