Sodium Chloride → ethyl 5,6,7,8-tetrahydro-11-acetoxymethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylate

HRID 1600648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1600648
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:9]2[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH2:16][N:7]3[C:8]=2[C:4]=1[CH:5]=[C:6]3[C:18]([O:20][CH2:21][CH3:22])=[O:19].[C:23]([O-:26])(=[O:25])[CH3:24].[K+].[Cl-].[Na+]>CN(C)C=O>[C:23]([O:26][CH2:2][C:3]1[CH:11]=[CH:10][C:9]2[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH2:16][N:7]3[C:8]=2[C:4]=1[CH:5]=[C:6]3[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:25])[CH3:24]

Komponenten

5

Edukt 3

HCID 5234Sodium ChlorideHCID 517044Potassium AcetateHCID 70238124ethyl 5,6,7,8-tetrahydro-11-bromomethyl-8-oxo-4H-azocino [3.2.1-hi]indole-2-carboxylate

Produkt 1

HCID 70235751ethyl 5,6,7,8-tetrahydro-11-acetoxymethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylateAusbeute 84,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of ethyl 5,6,7,8-tetrahydro-11-bromomethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylate (2.92 g, 8.02 mmol), potassium acetate (1.18 g, 12.0 mmol) and N,N-dimethylformamide (30 ml) was stirred at room temperature for 2.5 hours. The reaction mixture was poured into 10% aqueous sodium chloride solution and extracted with ethyl acetate. The extract was washed with 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off and the obtained residue was purified with silica gel column chromatography (eluated with ethyl acetate/n-hexane=1/5) to give 2.33 g of ethyl 5,6,7,8-tetrahydro-11-acetoxymethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylate.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 5% aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe obtained residue was purified with silica gel column chromatography (eluated with ethyl acetate/n-hexane=1/5)

Quellen und Nachweise

ORD-Eintrag
ord-4211b74bf604402e85db519ca0d68fad
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977100

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