Reaktion #47208

Reaktionsgleichung

sodium hydride

4-(2-Hydroxyacetyl)-3,3-dimethylpiperazin-2-one

sodium hydride

3-cyano-1,1,1-trifluoroprop-2-en-2-yl 4-methylbenzenesulfonate

→

4-(4-amino-2-(trifluoromethyl)furan-5-carbonyl)-3,3-dimethylpiperazin-2-one

Ausbeute 6.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturTo the resulting, cooled (0° C.) mixture
2. 2
   TemperaturThe reaction was gradually warmed up to 25° C.
3. 3
   workup.STIRRINGstirred for an additional 2 hours
4. 4
   workup.STIRRINGthe mixture stirred for another additional 4 hours
5. 5
   SonstigeThe reaction mixture was quenched with water
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   Sonstigethe combined organic layers dried
8. 8
   Sonstigethe crude product purified by preparative thin layer chromatography

Vorschrift

4-(2-Hydroxyacetyl)-3,3-dimethylpiperazin-2-one (0.090 g, 0.48 mmol) and sodium hydride (60%, 0.040 g, 0.97 mmol) were dissolved in 3 mL DMF and stirred at 25° C. for 30 min. To the resulting, cooled (0° C.) mixture was added drop-wise 3-cyano-1,1,1-trifluoroprop-2-en-2-yl 4-methylbenzenesulfonate (0.16 g, 0.56 mmol). The reaction was gradually warmed up to 25° C., stirred for an additional 2 hours, 2 additional equivalents of sodium hydride were added and the mixture stirred for another additional 4 hours. The reaction mixture was quenched with water, extracted with ethyl acetate, the combined organic layers dried, the solvent eliminated under vacuum and the crude product purified by preparative thin layer chromatography. (silicagel, dichloromethane:methanol 95:5) to afford 0.010 g of 4-(4-amino-2-(trifluoromethyl)furan-5-carbonyl)-3,3-dimethylpiperazin-2-one.

Quelle