Water → HCID 15063405, compound

HRID 863697Notes

Reaction equation

HRID 863697 reaction equation
[OH:1][C:2]1[C:7]2=[CH:8][C:9]3[C:14]([N:6]2[CH2:5][CH2:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=[CH:11][CH:10]=3.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CN(C)C=O>[CH2:18]([O:17][C:15]([C:3]1([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:4][CH2:5][N:6]2[C:14]3[C:9]([CH:8]=[C:7]2[C:2]1=[O:1])=[CH:10][CH:11]=[CH:12][CH:13]=3)=[O:16])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 54678585HCID 54678585, compound

Product 1

HCID 15063405HCID 15063405, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5 g of ethyl 6,7-dihydro-9-hydroxypyrido[1,2-a]indole-8-carboxylate (prepared as described in Example 1) in 200 ml of dimethylformamide was treated with 550 mg of sodium hydride. The mixture was stirred under a nitrogen atmosphere and then a solution of 3.6 g of ethyl bromoacetate in 50 ml of dimethylformamide was added. After 16 hours, the mixture was poured into water and extracted with diethyl ether. The combined extracts were washed with water, dried and concentrated to give 4.4 g of ethyl 8-(ethoxycarbonyl)-6,7,8,9-tetrahydro-9-oxopyrido[1,2-a]indole-8-acetate.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined extracts were washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f73de492cc5b45a9b37f7cebacd74f1d
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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