Ethyl bromoacetate → HCID 19095907, compound

HRID 486777Notes

Reaction equation

HRID 486777 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]1[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][N:17]12.Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>C1COCC1.CCCCCC>[CH2:29]([O:28][C:26]([C:23]1([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:22][N:17]2[C:18]3[C:14]([CH:15]=[C:16]2[CH2:25][CH2:24]1)=[CH:13][CH:21]=[CH:20][CH:19]=3)=[O:27])[CH3:30]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 7912DiisopropylamineHCID 15063410HCID 15063410, compoundHCID 178418339Butyllithium

Product 1

HCID 19095907HCID 19095907, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A stirred solution of 2.52 ml of diisopropylamine in 20 ml of THF was cooled in a bath at -78° C. under an argon atmosphere and treated with 11.25 ml of a 1.6M solution of n-butyllithium in n-hexane. The mixture was treated with a solution of 2.85 g of ethyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-7-carboxylate in 80 ml of THF. After 10 minutes, 1.46 ml of ethyl bromoacetate were added and the cooling bath was removed. The mixture was stirred and then diluted with diethyl ether. The solution was washed in succession with saturated aqueous ammonium chloride, water and sodium chloride solution and then dried. The solvent was removed by evaporation and the residue was subjected to chromatography on silica gel using ethyl acetate/n-hexane (1:9) for the elution to give 2.55 g of ethyl 7-(ethoxycarbonyl)-6,7,8,9-tetrahydropyrido-[1,2-a]indole-7-acetate.

Workup

  1. customthe cooling bath was removed
  2. additiondiluted with diethyl ether
  3. washThe solution was washed in succession with saturated aqueous ammonium chloride, water and sodium chloride solution
  4. customdried
  5. customThe solvent was removed by evaporation
  6. washfor the elution

Sources & evidence

ORD record
ord-2835e054df6e4db7912ef886818045f3
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

Loading…