Реакция #47208

Уравнение реакции

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

Выход 6.8%

Растворители

DMF

Условия реакции

Обработка

1. 1
   ТемператураTo the resulting, cooled (0° C.) mixture
2. 2
   ТемператураThe 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
   ДругоеThe reaction mixture was quenched with water
6. 6
   Экстракцияextracted with ethyl acetate
7. 7
   Другоеthe combined organic layers dried
8. 8
   Другоеthe crude product purified by preparative thin layer chromatography

Методика

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.

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