手性拆分制备R-(+)-α-硫辛酸
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摘要
报道了一种手性拆分外消旋硫辛酸的方法。以外消旋硫辛酸为原料,按一般的酸碱反应,与R-(+)-α-苯乙胺成非对映异构体盐;然后引入晶种重结晶得到单一手性的盐,后经酸化、重结晶制得R-(+)-α-硫辛酸,收率80%,R/S=99/1,其结构经~1H NMR和HR-MS(ESI)确证。
A chiral resolution to prepare R-(+)-α-lipoic acid was reported. To a solution of the salt of R-(+)-phenethylamine and racemic α-lipoic acid was added a small amount of the salt of R-(+)-α-phenethylamine and R-(+)-α-lipoic acid to induce recrystallization. The precipitate was collected to give the salt of R-(+)-α-phenethylamine and R-(+)-α-lipoic acid. After acidification and recrystallization, the optical purity R-(+)-α-lipoic acid was obtained in 80% yield with R/S=99/1. The structure was confirmed by ~1H NMR and HR-MS(ESI).
A chiral resolution to prepare R-(+)-α-lipoic acid was reported. To a solution of the salt of R-(+)-phenethylamine and racemic α-lipoic acid was added a small amount of the salt of R-(+)-α-phenethylamine and R-(+)-α-lipoic acid to induce recrystallization. The precipitate was collected to give the salt of R-(+)-α-phenethylamine and R-(+)-α-lipoic acid. After acidification and recrystallization, the optical purity R-(+)-α-lipoic acid was obtained in 80% yield with R/S=99/1. The structure was confirmed by ~1H NMR and HR-MS(ESI).
引文
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[4]BERNASCONI S,PIRNGRUBER G D,PRINS R.Influence of the properties of zeolite BEA on its performance in the nitration of toluene and nitrotoluene[J].Journal of Catalysis,2004,224(2):297-303.
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[10]FLAVIO V P,ANTONIO N P D,ANNIBALE F M,et al.Chain stitch multi-needle quilting machine and method to create a pattern in a quilting material:US20040002610[P].2004.
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[12]FLAVIO V P,ANTONIO N P D,ANNIBALE F M,et al.Chain stitch multi-needle quilting machine and method to create a pattern in a quilting material:US20040002610[P].2004.
[13]杨芹,冷一欣,林富荣,等.α-硫辛酸及其R型异构体的合成[J].常州大学学报(自然科学版),2009,21(4):20-23.
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