Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate → Methyl 2'-fluoro-2-(2-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662495

Reaction equation

HRID 1662495 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[C:20]1[C:24](=O)[CH2:23][CH2:22][C:21]=1[CH3:26]>[Pt](=O)=O.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[CH3:26]

Participants

4

Reactant 1

HCID 57705608Methyl 2'-fluoro-2-(2-methyl-5-oxo-1-cyclopenten-1-yl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706176Methyl 2'-fluoro-2-(2-methylcyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylateYield 13.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A screw-cap pressure tube was charged with 66.56B (0.31 g, 0.87 mmol), MeOH (10 mL), and platinum(IV) oxide (0.040 g, 0.17 mmol). The tube was purged three times with H2 at 45 psi and sealed, and the contents were stirred overnight. The mixture was diluted with EtOAc, filtered through silica gel (EtOAc), and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 69.33A (1:1 d.r.) (0.040 g) as a colorless oil.

Workup

  1. customThe tube was purged three times with H2 at 45 psi
  2. customsealed
  3. additionThe mixture was diluted with EtOAc
  4. filtrationfiltered through silica gel (EtOAc)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-b38c943dd6da45b6b7c5f9a6dac62e6f
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Linked notes

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