HCID 67212135, compound → HCID 178450673, compound

HRID 1401894Notes

Reaction equation

HRID 1401894 reaction equation
[C:1]([O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH2:29][CH2:28][CH:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:26][CH:25]=3)=[CH:20][CH:19]=2)[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([C:18]2[CH:19]=[CH:20][C:21]([C@H:24]3[CH2:25][CH2:26][C@@H:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:28][CH2:29]3)=[CH:22][CH:23]=2)[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67212135HCID 67212135, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178450673HCID 178450673, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-{(R)-2-[4-(4-tert-Butyl-cyclohex-1-enyl)-phenyl]-2-carboxy-ethyl}-benzoic acid tert-butyl ester (3.0 g) in ethyl acetate (100 mL) added 10% palladium on carbon (300 mg). The mixture was stirred under a balloon filled with hydrogen, until proton NMR indicated the disappearance of the olefinic signal. The reaction was filtered through a plug of celite, and the filtrate was concentrated under reduced pressure to give a mixture of cis/trans isomers (in a ratio of 1:1, based on 1H NMR). The cis1 and trans isomers were separated by reverse phase chromatography with the latter being cis (1.34 g, 2.9 mmol, 35%). 1H NMR (CDCl3): δ 0.95 (9H, s), 1.23-1.38 (4H, m), 1.58 (9H, s), 1.88-1.98 (4H, m), 2.39-2.56 (1H, m), 3.05-3.12 (1H, m), 3.19-3.50 (1H, m), 3.82-3.90 (1H, m), 7.19-7.22 (6H, m), 8.81 (2H, d).

Workup

  1. filtrationThe reaction was filtered through a plug of celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give
  4. additiona mixture of cis/trans isomers (in a ratio of 1:1
  5. customThe cis1 and trans isomers were separated by reverse phase chromatography with the latter

Sources & evidence

ORD record
ord-ace42229a3304ca3be8d5af9b3865de9
Source dataset
uspto-grants-2014_12
Patent number
US08907103B2

Reaction notes

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