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

HRID 650087Notes

Reaction equation

HRID 650087 reaction equation
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]

Participants

5

Reactant 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

Product 1

HCID 70235751ethyl 5,6,7,8-tetrahydro-11-acetoxymethyl-8-oxo-4H-azocino[3.2.1-hi]indole-2-carboxylateYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9d58d2621ee64f60be2df3c487a1bfc9
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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