ethyl 2-(2-oxo-1-pyrrolidinyl)butanoate -Drug Synthesis Database

【结构式】

【分子编号】61963

【品名】ethyl 2-(2-oxo-1-pyrrolidinyl)butanoate

【CA登记号】

【分子式】C₁₀H₁₇NO₃

【分子量】199.24992

【元素组成】C 60.28% H 8.6% N 7.03% O 24.09%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

The condensation of 2-pyrrolidone (I) with ethyl 2-bromobutyrate (II) by means of NaOEt in ethanol gives 2-(2-oxopyrrolidin-1-yl)butyric acid ethyl ester (III), which is hydrolyzed with NaOH to the corresponding acid (IV). The reaction of (IV) with SOCl2 affords the acyl chloride (V), which is treated with ammonia to provide the expected amide (VI). Alternatively, the reaction of acid (IV) with ammonia and thermolysis of the resulting ammonium salt also gives the butyramide (VI). Finally, the optical resolution of the racemic amide (VI) is performed by chiral HPLC.

参考文献中间体

合成目标

【1】 Gobert, J.; Geerts, J.-P.; Bodson, G. (UCB SA); (S)-alpha-Ethyl-2-oxopyrrolidineacetamide. AU 8542530; EP 0162036; ES 8608485; ES 8704893; US 4696943; US 4837223 .
【2】 Strubbe, J.H.L.; Linz, R.A. (UCB SA); New N-substd. lactams. DE 2106418 .
【3】 Cavoy, E.; Hamende, M.; Deleers, M.; Canvat, J.-P.; Zimmermann, V.; Futagawa, T. (Daicel Chemical Industries, Ltd.; UCB SA); Process for the preparation of levetiracetam. US 6107492 .
【4】 Cavoy, E.; Hamende, M.; Deleers, M.; Canvat, J.-P.; Zimmermann, V. (UCB SA); Process for preparing (S)- and (R)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide. US 6124473 .

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)	27397	2-Pyrrolidinone	616-45-5	C₄H₇NO	详情	详情
(II)	61962	DL-Ethyl 2-bromobutyrate; Ethyl 2-bromobutyrate; Ethyl 2-Bromobutyrate; DL-Ethyl-(2-brombutyrat); 2-Bromo-n-butyric Acid Ethyl Ester; Ethyl 2-Bromo-n-butyrate; 2-Bromobutyric acid ethyl ester; Ethyl-2-bromobutyrate; BNBE; alpha-Bromobutyric acid ethyl ester	533-68-6	C₆H₁₁BrO₂	详情	详情
(III)	61963	ethyl 2-(2-oxo-1-pyrrolidinyl)butanoate		C₁₀H₁₇NO₃	详情	详情
(IV)	11268	2-(2-Oxo-1-pyrrolidinyl)butyric acid	67118-31-4	C₈H₁₃NO₃	详情	详情
(V)	61964	2-(2-oxo-1-pyrrolidinyl)butanoyl chloride		C₈H₁₂ClNO₂	详情	详情
(VI)	61965	2-(2-oxo-1-pyrrolidinyl)butanamide		C₈H₁₄N₂O₂	详情	详情

Extended Information