Hydrochloric Acid → (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile

HRID 482070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482070
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]1([CH2:13][N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[C@H:11]([CH3:12])O1.[C-:19]#[N:20].C([Al+]CC)C.[OH2:26].Cl>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:26])([CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[C@@H:11]([CH3:12])[C:19]#[N:20]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 16686413Diethyl aluminum cyanide

Produkt 1

HCID 9860445(2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution with 5 g (20.0 mmol) of optically active (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane dissolved in 40 ml of toluene, were added 80 ml of diethylaluminum cyanide (1.0M toluene solution) in a nitrogen atmosphere. The mixture was heated at 50° C. for 12 hours, and 10 ml of water and 120 ml of 1N HCl were successively added dropwise thereto. The resulting mixture was stirred for 2 hours at room temperature, filtered through a Florisil pad and then subjected to extraction with ethyl acetate. The resultant organic layer was washed 4 times with a liquid obtained by mixing water and saturated saline at a ratio of 1:1, and finally with saturated saline. After the solvent was distilled out under reduced pressure, the residue was washed with diisopropyl ether, thereby obtaining 3.15 g (56.6%) of optically active (2S,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile. Physical properties of this product are described below.

Aufarbeitung

  1. filtrationfiltered through a Florisil pad
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe resultant organic layer was washed 4 times with a liquid
  4. customobtained
  5. distillationAfter the solvent was distilled out under reduced pressure
  6. washthe residue was washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9f14598334ca4d14ab123f86b08d530c
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792781

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