Reaktion #943487

Reaktionsgleichung

(S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethoxyphenyl)piperazin-1-yl]propan-2-ol

sodium hydride

→

(S)-2-[4-(4-trifluoromethoxyphenyl)piperazin-1-yl]methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

Ausbeute 48.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith cooling on ice-bath
2. 2
   Temperaturunder reflux for 6 hours
3. 3
   EinengenThe reaction mixture was concentrated under reduced pressure
4. 4
   workup.ADDITIONthe residue was added water and ethyl acetate
5. 5
   FiltrationThe precipitates were filtered off
6. 6
   Sonstigepurified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)
7. 7
   Sonstigerecrystallized from isopropanol

Vorschrift

To a solution of (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-[4-(4-trifluoromethoxyphenyl)piperazin-1-yl]propan-2-ol prepared in Example 369 (5.85 g, 12.61 mmol) in THF (150 ml), sodium hydride (0.66 g, 18.92 mmol) was added with cooling on ice-bath followed by stirring under reflux for 6 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added water and ethyl acetate. The precipitates were filtered off, purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) and recrystallized from isopropanol to afford (S)-2-[4-(4-trifluoromethoxyphenyl)piperazin-1-yl]methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (2.58 g, yield 48%) as a light yellow solid.

Quelle