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

Reaktionsgleichung

Reaktionsgleichung von HRID 1662451
[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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 57706805Methyl 2'-fluoro-2-(2-methyl-5-oxocyclopentyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylateAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-67ac87e675cf4f59b626f4fa626bf202
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

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