Methyl 2-(5,5-dimethyl-1-cyclopenten-1-yl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylate → Methyl 2-(2,2-dimethylcyclopentyl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662510Notes

Reaction equation

HRID 1662510 reaction equation
[CH3:1][C:2]1([CH3:25])[C:6]([C:7]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=[CH:5][CH2:4][CH2:3]1>CCOC(C)=O.[Pd]>[CH3:1][C:2]1([CH3:25])[CH2:3][CH2:4][CH2:5][CH:6]1[C:7]1[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:8]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1

Participants

4

Reactant 1

HCID 57707227Methyl 2-(5,5-dimethyl-1-cyclopenten-1-yl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706985Methyl 2-(2,2-dimethylcyclopentyl)-3'-(methyloxy)-1,1'-biphenyl-4-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 78.5A (0.50 g, 1.5 mmol) in EtOAc (2.00 mL) at 23° C. was added palladium on carbon (0.16 g, 1.5 mmol). The reaction was placed under an atmosphere of hydrogen and stirred for 19 hours. The reaction mixture was then filtered and the filtrate was concentrated in vacuo. The product was purified on silica gel (0-10% EtOAc in hexanes) to yield 78.5B as a colorless oil (0.50 g, 99% yield).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe product was purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-197ce3d117b44024a28fb3345a4abed0
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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