반응 #47208

반응 방정식

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

수율 6.8%

용매

DMF

반응 조건

후처리

1. 1
   온도To the resulting, cooled (0° C.) mixture
2. 2
   온도The 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
   기타The reaction mixture was quenched with water
6. 6
   추출extracted with ethyl acetate
7. 7
   기타the combined organic layers dried
8. 8
   기타the crude product purified by preparative thin layer chromatography

실험 절차

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.

출처