Jean-Christophe Carry, Eric Brohan, Sébastien Perron
Nov 21, 2013
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Journal
Organic Process Research & Development
Abstract
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 (−)-tert-butyl-3-hydroxyazepane-1-carboxylate into known (R)-(−)-benzyl-3-hydroxyazepane-1-carboxylate.