HCID 54737460, compound → HCID 23362645, compound

HRID 1081535Notes

Reaction equation

HRID 1081535 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9](O)[C:10]=1[OH:11])=[O:5])[CH3:2]>OS(O)(=O)=O.[Rh]>[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([OH:11])[CH2:9][CH:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 54737460HCID 54737460, compound

Product 1

HCID 23362645HCID 23362645, compound

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 1118Sulfuric AcidSolvent

Procedure

2,5-Bis-ethoxycarbonyl-3,4-dihydroxypyrrole (1.0 g, 4.1 mmol) was dissolved in 3% ethanolic H2SO4 (50 ml). Rhodium on carbon (5%) (1.0 g) was added and the reduction reaction was allowed to run under hydrogen (9.4 bar) at 80° C. overnight. The catalyst was filtered off and the solvent evaporated. The reaction mixture was dissolved in water, the pH was adjsusted with Na2CO3, and extracted with dichloromethane. The crude mixture was chromatographed on silica and the title product was isolated. Yield: 0.2 g (21%), FAB-MS: 232 (M+1).

Workup

  1. customthe reduction reaction
  2. filtrationThe catalyst was filtered off
  3. customthe solvent evaporated
  4. dissolutionThe reaction mixture was dissolved in water
  5. extractionextracted with dichloromethane
  6. customThe crude mixture was chromatographed on silica

Sources & evidence

ORD record
ord-6387f2460dd94608aa3a4986c70ba055
Source dataset
uspto-grants-1996_12
Patent number
US05587144

Reaction notes

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