Sodium hydride → 1-(4-Methyl-2-pyridyl)-4-[(E)-3,3,4,4,4-pentafluorobut-1-enyl]sulfonyl-piperazine

HRID 1775346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1775346
C(OP([CH2:9][S:10]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)[CH2:15][CH2:14]1)(=[O:12])=[O:11])(OCC)=O)C.[H-].[Na+].[F:28][C:29]([F:38])([C:34]([F:37])([F:36])[F:35])[CH:30](OC)O>C1COCC1>[CH3:25][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([N:16]2[CH2:15][CH2:14][N:13]([S:10](/[CH:9]=[CH:30]/[C:29]([F:38])([F:28])[C:34]([F:37])([F:36])[F:35])(=[O:11])=[O:12])[CH2:18][CH2:17]2)[CH:24]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1084041-Propanol, 2,2,3,3,3-pentafluoro-1-methoxy-HCID 898258041-(Diethoxyphosphorylmethylsulfonyl)-4-(4-methyl-2-pyridyl)piperazine

Produkt 1

HCID 717652901-(4-Methyl-2-pyridyl)-4-[(E)-3,3,4,4,4-pentafluorobut-1-enyl]sulfonyl-piperazineAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(diethoxyphosphorylmethylsulfonyl)-4-(4-methyl-2-pyridyl)piperazine (242 mg, 0.618 mmol) in anhydrous THF (25 ml) were added molsieves 4A and sodium hydride (60%, 38 mg, 0.95 mmol) under nitrogen and the mixture was stirred at room temperature for 10 minutes. The mixture was cooled to 0° C. and 2,2,3,3,3-pentafluoro-1-methoxy-propan-1-ol (300 mg, 1.67 mmol) was added. The mixture was stirred at 0° C. for 30 minutes and then allowed to reach room temperature over one hour. The mixture was filtered through kieselguhr, concentrated under reduced pressure and the residue was purified by column chromatography (reveleris, gradient from 0 to 100% ethyl acetate in n-heptane) to yield 130 mg (0.337 mmol, yield 55%).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe mixture was stirred at 0° C. for 30 minutes
  3. waitto reach room temperature over one hour
  4. filtrationThe mixture was filtered through kieselguhr
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by column chromatography (reveleris, gradient from 0 to 100% ethyl acetate in n-heptane)
  7. customto yield 130 mg (0.337 mmol, yield 55%)

Quellen und Nachweise

ORD-Eintrag
ord-2d59096a40f84be398e9ce6559225744
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260441B2

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