5-Trifluoromethyl-6-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester → 5-Ethyl-6-trifluoromethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 225594Notes

Reaction equation

HRID 225594 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH:21]=[CH2:22])=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]2[C:15](=[CH:14][C:13]([C:17]([F:20])([F:18])[F:19])=[C:12]([CH2:21][CH3:22])[CH:11]=2)[CH2:16]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 577533965-Trifluoromethyl-6-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

Product 1

HCID 577535725-Ethyl-6-trifluoromethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl esterYield 20%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution 0.54 mmol 5-trifluoromethyl-6-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester in 50 ml methanol was added 50 mg 10% palladium on charcoal and the mixture was stirred under an atmosphere of hydrogen (0.6 bar positive pressure) for 72 h. The reaction mixture was then filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid (20% yield). MS (m/e): 260.0 ([M+H−Me2C═CH2]+, 100%).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-93e5d97d604e41a2a274c3447199d777
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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