2-Cyano-3-methyl-4-oxo-4-(2-trifluoromethyl-phenyl)-butyric acid methyl ester → HCID 67254019, compound

HRID 383747Notes

Reaction equation

HRID 383747 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:19]#[N:20])[CH:5]([CH3:18])[C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14]>C(O)=O.[Ni].C(Cl)Cl>[CH3:1][O:2][C:3]([CH:4]1[C:5]([CH3:18])=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])[NH:20][CH2:19]1)=[O:21]

Participants

5

Reactant 1

HCID 598075352-Cyano-3-methyl-4-oxo-4-(2-trifluoromethyl-phenyl)-butyric acid methyl ester

Product 1

HCID 67254019HCID 67254019, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyano-3-methyl-4-oxo-4-(2-trifluoromethyl-phenyl)-butyric acid methyl ester (13.27 g, 44.4 mmol) in formic acid (100 mL) was added freshly prepared Raney nickel [Al—Ni (1:1), 117 g] and the mixture was heated to reflux with stirring for 2 h. After cooling, the catalyst was removed by filtration and washed with ethanol. The combined filtrates were concentrated to give an oil, which was re-dissolved in DCM and filtered to remove residual solids. Evaporation of solvent gave 4-methyl-5-(2-trifluoromethyl-phenyl)-2,3-dihydro-1H-pyrrole-3-carboxylic acid methyl ester as an oil (10 g, 79%), which was used in the next step without purification. MS (ES): 286 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. customthe catalyst was removed by filtration
  5. washwashed with ethanol
  6. concentrationThe combined filtrates were concentrated
  7. customto give an oil, which
  8. filtrationfiltered
  9. customto remove residual solids
  10. customEvaporation of solvent

Sources & evidence

ORD record
ord-5f8b50e898764f64a7e8b884e1cf2e25
Source dataset
uspto-grants-2013_02
Patent number
US08367667B2

Reaction notes

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