Chiral Supercritical Fluid Chromatography in the Preparation of Enantiomerically Pure (S)-(+)-tert-Butyl-3-hydroxyazepane-1-carboxylate

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• 作者：Jean-Christophe Carry ; Eric Brohan ; S茅bastien Perron ; Pierre-Eric Bardouillet
• 刊名：Organic Process Research & Development
• 出版年：2013
• 出版时间：December 20, 2013
• 年：2013
• 卷：17
• 期：12
• 页码：1568-1571
• 全文大小：214K
• 年卷期：v.17,no.12(December 20, 2013)
• ISSN：1520-586X

文摘

We report herein the isolation and characterization of (S)-(+)-tert-butyl-3-hydroxyazepane-1-carboxylate via resolution of the commercially available racemate, using chiral supercritical fluid chromatography (SFC). After optimization of the experimental chromatographic conditions, preparative scale separation using a stacked injections protocol led to 10.5 g of the dextrogyre enantiomer. Assignment of the absolute stereochemistry of the latter was accomplished by transforming (鈭?-tert-butyl-3-hydroxyazepane-1-carboxylate into known (R)-(鈭?-benzyl-3-hydroxyazepane-1-carboxylate.