Ammonium formate → HCID 19095961, compound

HRID 486775Notes

Reaction equation

HRID 486775 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:17][N:9]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH:16]=[C:8]2[C:7]1=[O:18])=[O:5])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:17][N:9]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH:16]=[C:8]2[CH:7]1[OH:18])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 15063404HCID 15063404, compound

Product 1

HCID 19095961HCID 19095961, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 17.7 g of ethyl 2-(ethoxy-carbonyl)-2,3-dihydro-1-oxo-1H-pyrrolo[1,2-a]indole-2-acetate in 200 ml of methanol was treated under a nitrogen atmosphere with 1.5 g of 10% palladium-on-charcoal and 10 g of ammonium formate. The mixture was heated at reflux for 1.5 hours, then cooled and filtered. The filtrate was concentrated and the residue was partitioned between ethyl acetate and water. The organic layer was washed with sodium chloride solution and dried. Evaporation of the solvent gave 16.5 g of ethyl 2-(ethoxycarbonyl)-2,3-dihydro-1-hydroxy-1H-pyrrolo[1,2-a]indole-2-acetate

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was partitioned between ethyl acetate and water
  7. washThe organic layer was washed with sodium chloride solution
  8. customdried
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b08751123b484f6eabc5100e727818ba
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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