HCID 178499654, compound → 4-(2-Methoxycarbonylethyl)bicyclo[2.2.2]octane-1-carboxylic acid

HRID 2105697Notes

Reaction equation

HRID 2105697 reaction equation
C([O:8][C:9]([C@:11]12[CH2:18][CH2:17][C@@:14]([CH:19]=[CH:20][C:21]([O:23][CH3:24])=[O:22])([CH2:15][CH2:16]1)[CH2:13][CH2:12]2)=[O:10])C1C=CC=CC=1>C(O)C.O.[Pd]>[CH3:24][O:23][C:21]([CH2:20][CH2:19][C:14]12[CH2:15][CH2:16][C:11]([C:9]([OH:10])=[O:8])([CH2:18][CH2:17]1)[CH2:12][CH2:13]2)=[O:22]

Participants

4

Reactant 1

HCID 178499654HCID 178499654, compound

Product 1

HCID 166564244-(2-Methoxycarbonylethyl)bicyclo[2.2.2]octane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

4-(2-Methoxycarbonyl-vinyl)-bicyclo[2.2.2]octane-1-carboxylic acid benzyl ester (XX, Example 95, 35 g, 106.6 mmol) is dissolved in ethyl alcohol/water (9/1, 300 ml) and is placed in a Porter pressure bottle. Palladium on carbon (10%, 5 g) is added and the mixture is hydrogenated (65 psi) for 48 hr. The reaction mixture is filtered through a pad of celite and the combined filtrates were concentrated to give the title compound, NMR (400 MHz, CDCl3) δ 3.58, 2.18, 1.74, 1.44 and 1.38.

Workup

  1. customfor 48 hr
  2. filtrationThe reaction mixture is filtered through a pad of celite
  3. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-303fd94ab53d4935a4953199bfce8d89
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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