Citation: Liu Bin, Xu Xiaona, Tong Hongjuan, Zhu Zhoujing. Synthesis of N-Substituted-5-oxopyrrolidine-3-carboxylic Acids[J]. Chemistry, ;2019, 82(9): 821-825. shu

Synthesis of N-Substituted-5-oxopyrrolidine-3-carboxylic Acids

School of Pharmacy, Shaanxi Institute of International Trade & Commerce, Xi'an 712046;Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province, Xi'an 712046

Received Date: 11 May 2019
Accepted Date: 15 June 2019

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Three kinds of methyl N-substituted-5-oxopyrrolidine-3-carboxylate (2a~2c) were synthesized by a Michael addition reaction of dimethyl itaconate and three types of alcyl amines respectively, and they were further hydrolyzed under basic conditions to afford three N-substituted-5-oxopyrrolidine-3-carboxylic acids (1a~1c). The structure of the products and intermediates were confirmed by ¹H NMR, ¹³C NMR and ESI-MS. Taking the Michael addition reaction of dimethyl itaconate and cyclobutylamine as a model, the optimized reaction process of this step was finally determined as follows:n(cyclobutanamine):n(dimethyl itaconate)=1.3:1, reacting in toluene at 110℃ for 2 h. Compound 2b was obtained in a yield of 91.2%, and its structure was further confirmed by X-ray single crystal diffraction.
- N-substituted-5-oxopyrrolidine-3-carboxylic acid,
- 2-Pyrrolidine derivatives,
- Michael addition reaction,
- Crystal structure
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