3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)4-hydroxy-phenyl]-acrylic acid tert-butyl ester → HCID 58979464, compound

HRID 1181052Notes

Reaction equation

HRID 1181052 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:27])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:28])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][N:17]1[C:18](=[O:27])[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]1=[O:26])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 687431663-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)4-hydroxy-phenyl]-acrylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 58979464HCID 58979464, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A 1 gallon autoclave was charged with 3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-hydroxy-phenyl]-acrylic acid tert-butyl ester (196 g, 0.517 mol), ethyl acetate (2.6 L) and 5% palladium on carbon (75 g). The autoclave was kept at 25° C. under 60 psi of hydrogen for 21 h. The temperature of the reaction was increased to 40° C., and the pressure was increased to 75 psi for 5 h. The mixture was filtered through a pad of hyflo and concentrated to the title compound (186 g, 94.4%): MS (ESI) m/z 380.2 (M−H)−.

Workup

  1. temperaturethe pressure was increased to 75 psi for 5 h
  2. filtrationThe mixture was filtered through a pad of hyflo
  3. concentrationconcentrated to the title compound (186 g, 94.4%)

Sources & evidence

ORD record
ord-12b6d64ed9e140e6ac6f05a52bfe38e0
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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