HCID 54737460, compound → HCID 23362645, compound

HRID 1755964Notes

Reaction equation

HRID 1755964 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-dihydroxypyrrol (1.0 g, 4.1 mmol) was dissolved in ethanolic H2SO4 (3%) (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 adjusted 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-c21b672bfaa146399bcc1708ccb80439
Source dataset
uspto-grants-1995_08
Patent number
US05439668

Reaction notes

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