HCID 14456189, compound → HCID 14456190, compound

HRID 1249372Notes

Reaction equation

HRID 1249372 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([N+:23]([O-])=O)[CH:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:19][O:20][CH2:21][CH3:22])[NH:12][CH:11]=1)[CH2:7][O:8][CH3:9])[CH3:2]>C(O)C.[Ni]>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([NH2:23])[CH:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:19][O:20][CH2:21][CH3:22])[NH:12][CH:11]=1)[CH2:7][O:8][CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 14456189HCID 14456189, compound

Product 1

HCID 14456190HCID 14456190, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Ethyl-3-(4-ethoxymethylindol-3-yl)-4-methoxy-2-nitrobutyrate (11.1 g) in ethanol (350 ml) was catalytically hydrogenated with Raney-nickel at room temperature under atmospheric pressure. The product obtained after filtration of the catalyst and evaporation of the solvent, was dissolved in a mixture of diethylether and ethylacetate. The solution was treated with water and evaporated. 8 g of oily ethyl-2-amino-3-(4-ethoxymethylindol-3-yl)-4-methoxybutyrate were obtained.

Workup

  1. customThe product obtained
  2. filtrationafter filtration of the catalyst and evaporation of the solvent
  3. dissolutionwas dissolved in a mixture of diethylether and ethylacetate
  4. additionThe solution was treated with water
  5. customevaporated

Sources & evidence

ORD record
ord-67548293a29249b697d0f64be4cffa50
Source dataset
uspto-grants-1986_12
Patent number
US04631285

Reaction notes

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