Hydrochloric Acid → 3-(4,4-difluoro-3-methylene-3,4-dihydro-2H-pyrrol-5-yl)-2-(trifluoromethyl)pyridine

HRID 1426693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426693
[F:1][C:2]([F:26])([C:14](=O)[C:15]1[C:16]([C:21]([F:24])([F:23])[F:22])=[N:17][CH:18]=[CH:19][CH:20]=1)[C:3](=[CH2:13])[CH2:4][NH:5]C(=O)OC(C)(C)C.Cl>C(O)(=O)C>[F:1][C:2]1([F:26])[C:14]([C:15]2[C:16]([C:21]([F:24])([F:23])[F:22])=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:5][CH2:4][C:3]1=[CH2:13]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59826893HCID 59826893, Verbindung

Produkt 1

HCID 598268813-(4,4-difluoro-3-methylene-3,4-dihydro-2H-pyrrol-5-yl)-2-(trifluoromethyl)pyridineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl {3,3-difluoro-2-methylene-4-oxo-4-[2-(trifluoromethyl)pyridin-3-yl]butyl}carbamate (3.25 g) in acetic acid (10 mL) was added dropwise concentrated hydrochloric acid (3 mL). The obtained mixture was stirred at room temperature for 2 hr, and concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=3:1) to give the title compound as a yellow oil (yield 1.85 g, 83%).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionSaturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-9949bf2518124358ba8426c940446693
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933105B2

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