1,5,6,7-Tetrahydro-4H-indol-4-one → 1-[4-(2,3-Dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1,5,6,7-tetrahydroindol-4-one

HRID 400691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400691
[CH3:1][C:2]([C:12]1[C:20]2[O:19][CH2:18][CH2:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH2:3][C:4]1([C:7]([F:10])([F:9])[F:8])[CH2:6][O:5]1.[NH:21]1[C:29]2[CH2:28][CH2:27][CH2:26][C:25](=[O:30])[C:24]=2[CH:23]=[CH:22]1.[O-]CC.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[O:19]1[C:20]2[C:12]([C:2]([CH3:1])([CH3:11])[CH2:3][C:4]([OH:5])([C:7]([F:8])([F:10])[F:9])[CH2:6][N:21]3[C:29]4[CH2:28][CH2:27][CH2:26][C:25](=[O:30])[C:24]=4[CH:23]=[CH:22]3)=[CH:13][CH:14]=[CH:15][C:16]=2[CH2:17][CH2:18]1

Komponenten

6

Edukt 4

HCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 577755187-[1,1-Dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran

Produkt 1

HCID 600264231-[4-(2,3-Dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1,5,6,7-tetrahydroindol-4-oneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a suspension of 7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran (59.2 mg, 0.21 mmol) and 1,5,6,7-tetrahydroindol-4-one (56.0 mg, 0.41 mmol) in 0.4 mL of anhydrous ethanol was added 0.077 mL of sodium ethoxide solution (21 wt % in ethanol). The reaction mixture was then heated at 85° C. for 16 hours. The resulting mixture was poured into half-saturated sodium bicarbonate and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (eluted with 35% ethyl acetate-hexanes) to give 58.4 mg (66% yield) of the title compound as a white solid, m.p. 145° C.-146° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (eluted with 35% ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b077ed2160254a968b0fff0f79d3f0f8
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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