Ethyl Acetate → HCID 69742409, compound

HRID 1760367Notes

Reaction equation

HRID 1760367 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH2:25])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2].[H][H].C(OCC)(=[O:35])C>[Pd]>[CH2:1]([O:3][C:4]([C:6]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:10][CH2:9][C:8](=[O:35])[N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH3:25])=[CH:22][CH:23]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 69743649HCID 69743649, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69742409HCID 69742409, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 1-[6-(4-vinyl-phenoxy)-pyridin-3-yl]-pyrrolidine-2,2-dicarboxylic acid diethyl ester (0.20 g), 50 mg of 10% palladium on charcoal and 20 mL of ethyl acetate was shaken under 50 psi of hydrogen gas for 2 hours. The mixture was filtered and concentrated in vacuo, affording 0.20 g of 1-[6-(4-ethyl-phenoxy)-pyridin-3-yl]-5-oxo-pyrrolidine-2,2-dicarboxylic acid diethyl ester as a colorless syrup. 1H NMR (CDCl3, 500 MHz): 8.08 (d, 1H, J=2.5 Hz), 7.73 (dd, 1H, J=2.5, 8.5 Hz), 7.24 (d, 2H, J=7.5 Hz), 7.05 (d, 2H, J=8.0 Hz), 6.89 (d, 1H, J=9.0 Hz), 4.21 (q, 4H, J=7.0 Hz), 2.74 (m, 2H), 2.65 (m, 4H), 1.27 (t, 3H, J=8.0 Hz), 1.20 (t, 6H, J=7.5 Hz) ppm.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8fa1f7b421149eca8621ab9f0f5378d
Source dataset
uspto-grants-2005_01
Patent number
US06841671B2

Reaction notes

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