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《Information Recording Materials》 2009-01
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Simple Total Synthesis of 1-Carbethoxy-2-Methyl-4-Piperidone

XING Chun-yong,SUN Xiao-ai,GAO Min,ZHANG Wen-qin(Department of Chemistry,School of Science,Tianjin 300072,china)  
Through esterification,Michael addition,Dieckmann condensation,hydrolysis and decarboxylation,the title compound was synthesized from ammonia,crotonic acid,ethyl acrylate and ethyl chloroformate.First of all,the But-2-enoic acid ethyl ester was synthesized by esterification.And then the reaction of But-2-enoic acid ethyl ester with ammonia generated 3-Amino-butyric acid ethyl ester,which could react with acrylic acid ethyl ester through Michael addition to obtain asymmetry diester.The asymmetry diester that protected by ethoxycarbonyl could generated 3-[ethoxycarbonyl-(2-ethoxycarbonyl-ethyl)-amino]-butyric acid ethyl ester through intermolecular Dieckmann condensation.Finally,the title compound was obtained by the hydrolysis and decarboxylation of 3-[3thoxycarbonyl-(2-ethoxycarbonyl-ethyl)-amino-butyric acid ethyl ester.By optimizing reaction conditions,greatly enhanced the yield of the goal product.The advantages of this method are high yield and simple work-up.
【Fund】: 国家自然科学基金资助项目(20702037)
【CateGory Index】: TQ253
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