Methanol → Methyl 2-(2,2-dimethylcyclopentyl)-5'-(ethyloxy)-2'-fluoro-1,1'-biphenyl-4-carboxylate

HRID 1662410Notes

Reaction equation

HRID 1662410 reaction equation
[CH3:1][C:2]1([CH3:27])[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]=[C:21]([O:23][CH2:24][CH3:25])[CH:20]=[CH:19][C:18]=2[F:26])=[CH:5][CH2:4][CH2:3]1.CO>[Pd]>[CH3:27][C:2]1([CH3:1])[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]=[C:21]([O:23][CH2:24][CH3:25])[CH:20]=[CH:19][C:18]=1[F:26]

Participants

4

Reactant 2

HCID 887MethanolHCID 57705826Methyl 2-(5,5-dimethyl-1-cyclopenten-1-yl)-5'-(ethyloxy)-2'-fluoro-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57705774Methyl 2-(2,2-dimethylcyclopentyl)-5'-(ethyloxy)-2'-fluoro-1,1'-biphenyl-4-carboxylateYield 99.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a stirred solution of 66.25A (0.400 g, 1.09 mmol) in MeOH (10.00 mL, 1.09 mmol) at 23° C. was added palladium on carbon (0.116 g, 1.09 mmol). The reaction was placed under an atmosphere of hydrogen and stirred for 23 hours. The mixture was then filtered and concentrated in vacuo. The initial product was then purified on silica gel (0-20% EtOAc in hexanes) to yield 66.25B as a colorless oil (0.400 g, 99.5% yield).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe initial product was then purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8f73f9c0736e4569af28601dee97f673
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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