Cyclopentylhydrazine hydrochloride → Cyclopentyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 12891

Reaktionsgleichung

Reaktionsgleichung von HRID 12891
Cl.[CH:2]1([NH:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:9]([O:11][C:12](=[O:24])[C:13](=[CH:20]N(C)C)[C:14](=O)[C:15]([F:18])([F:17])[F:16])[CH3:10].C([O-])(=O)C.[Na+]>C(O)C>[CH2:9]([O:11][C:12]([C:13]1[CH:20]=[N:8][N:7]([CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)[C:14]=1[C:15]([F:16])([F:17])[F:18])=[O:24])[CH3:10]

Komponenten

5

Edukt 3

HCID 212349Cyclopentylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 53979199Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl ester

Produkt 1

HCID 63235074Cyclopentyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl esterAusbeute 52,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Cyclopentyl-hydrazine hydrochloride (0.250 g, 1.83 mmol, Example 64, Step 2), 2-dimethylaminomethylene-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester (0.403 g, 1.68 mmol) and anhydrous sodium acetate (0.163 g, 1.99 mmol) were combined in ethanol (2.5 mL) and heated at 70° C. for 17 hours. After cooling to room temperature, the reaction mixture was partitioned between methylene chloride and water. The organic phase was washed with water and brine. Each aqueous phase was back extracted with a second portion of methylene chloride. The two organic phases were combined, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography, eluting with a 10-40% ethyl acetate-hexanes gradient, yielded 1-cyclopentyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.244 g, 52%). Mass spectrum: m/z: 277.1 (M+H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between methylene chloride and water
  3. washThe organic phase was washed with water and brine
  4. extractionEach aqueous phase was back extracted with a second portion of methylene chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography
  8. washeluting with a 10-40% ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c4b6d49295c04785a4247f88d64849e0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728029B2

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