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Ethyl bromoacetate → Ethyl 2-[2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]ethyl]-6-cyano-1-indoleacetate

HRID 361924
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 361924
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]3[NH:23][C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[C:26]([C:31]#[N:32])[CH:25]=4)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].[Cl-].[NH4+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][C:22]3[N:23]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[C:26]([C:31]#[N:32])[CH:25]=4)=[CH:18][CH:19]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 571791022-[2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]ethyl]-6-indolecarbonitrile

Produkt 1

HCID 57010292Ethyl 2-[2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]ethyl]-6-cyano-1-indoleacetate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.4 g of 2-[2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]ethyl]-6-indolecarbonitrile was dissolved in 50 ml of N,N-dimethylformamide. 300 mg of 60% sodium hydride was added to the thus prepared solution during stirring under ice cooling, and the resulting mixture was warmed up to room temperature and stirred at the same temperature for 20 minutes. 0.76 ml of ethyl bromoacetate was added to the above mixture during stirring under ice cooling, followed by stirring for 1 hour. The resulting reaction solution was mixed with an ammonium chloride aqueous solution and extracted with a toluene/ethyl acetate mixture, and the resulting organic layer was washed with water and dried. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using a dichloromethane/acetone mixture as an elution solvent. In this way, 2.3 g of the title compound was obtained in a viscous and oily form.

Aufarbeitung

  1. stirringstirred at the same temperature for 20 minutes
  2. stirringduring stirring under ice cooling
  3. stirringby stirring for 1 hour
  4. customThe resulting reaction solution
  5. extractionextracted with a toluene/ethyl acetate mixture
  6. washthe resulting organic layer was washed with water
  7. customdried
  8. distillationAfter distilling off the solvent
  9. customthe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-b66118fd28fd41368cef1e15cab3e3b4
Quelldatensatz
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05866577

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