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【结 构 式】 
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【分子编号】32715 【品名】Ethyl 2-(2,4-dioxo-1-pyrrolidinyl)acetate; Ethyl pyrrolidine-2,4-dione-1-acetate 【CA登记号】 |
【 分 子 式 】C8H11NO4 【 分 子 量 】185.17968 【元素组成】C 51.89% H 5.99% N 7.56% O 34.56% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of ethyl iminodiacetate (I) with 2-ethoxycarbonylacetyl chloride (II) by means ot triethylamine in refluxing methylene chloride gives ethyl N-(2-ethoxycarbonylacetyl)iminodiacetate (III), which is cyclized by means of sodium ethoxide in refluxing ethanol yielding ethyl 4-hydroxy-3-(ethoxycarbonyl)-DELTA3-pyrrolin-2-one-1-acetate (IV). The isomerization of (IV) with water in refluxing acetonitrile affords ethyl pyrrolidine-2,4-dione-1-acetate (V), which is reduced with NaBH4 in dimethoxyethane to ethyl 4-hydroxypyrrolidine-2-one-1-acetate (VI). Finally, this compound is treated with ammonia in methanol.
| 【1】 Pifferi, G.; Pinza, M.; Cyclic GABA [4-aminobutyric acid]-GABOB[4-amino-3-hydroxybutyric acid] analogs. I. Synthesis of new 4-hydroxy-2-pyrrolidinone derivatives. Farmaco 1977, 32, 8, 602-613. |
| 【2】 Pifferi, G.; Pinza, M. (ISF SpA); Pyrrolidine derivatives. DE 2635853; FR 2320741; GB 1550160; NL 7608946; US 4118396 . |
| 【3】 de Angelis, L.; Blancafort, P.; Serradell, M.N.; Castaner, J.; Oxiracetam. Drugs Fut 1980, 5, 8, 405. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 32712 | Ethyl 2-[(2-ethoxy-2-oxoethyl)amino]acetate; Ethyl iminodiacetate | 6290-05-7 | C8H15NO4 | 详情 | 详情 |
| (II) | 13188 | ethyl 3-chloro-3-oxopropanoate; 2-Ethoxycarbonylacetyl chloride; Ethyl malonyl chloride | 36239-09-5 | C5H7ClO3 | 详情 | 详情 |
| (III) | 32713 | Ethyl 3-[bis(2-ethoxy-2-oxoethyl)amino]-3-oxopropanoate; N-(2-Ethoxycarbonylacetyl)iminodiacetate | C13H21NO7 | 详情 | 详情 | |
| (IV) | 32714 | Ethyl 4-hydroxy-3-(ethoxycarbonyl)-delta3-pyrrolin-2-one-1-acetate; Ethyl 1-(2-ethoxy-2-oxoethyl)-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate | C11H15NO6 | 详情 | 详情 | |
| (V) | 32715 | Ethyl 2-(2,4-dioxo-1-pyrrolidinyl)acetate; Ethyl pyrrolidine-2,4-dione-1-acetate | C8H11NO4 | 详情 | 详情 | |
| (VI) | 32716 | Ethyl 2-(4-hydroxy-2-oxo-1-pyrrolidinyl)acetate; Ethyl 4-hydroxypyrrolidine-2-one-1-acetate | C8H13NO4 | 详情 | 详情 |