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

HRID 1662451

Reaction equation

HRID 1662451 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:25])[CH2:23][CH2:22][C:21]=1[CH3:26]>[Pd].CCOC(C)=O>[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[C:24](=[O:25])[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 57706805Methyl 2'-fluoro-2-(2-methyl-5-oxocyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylateYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A pressure tube was charged with 66.56B (0.72 g, 2.0 mmol), EtOAc (20 mL), and Pd/C (10 wt. %) (0.22 g, 0.20 mmol). The tube was purged three times with H2 at 45 psi and sealed, and the contents were stirred for 48 hours. The mixture was filtered through silica gel (EtOAc) and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 66.56C (mixture of diastereomers) (0.63 g, 87% yield) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-67ac87e675cf4f59b626f4fa626bf202
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Linked notes

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