A. Carnell, R. Head, D. Bassett
Mar 8, 2004
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Influential Citations
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Journal
Tetrahedron-asymmetry
Abstract
Abstract A three step method for the large scale preparation of enantiomerically pure ethyl ( S )-3-hydroxybutyrate is reported starting from the commercial biopolymer poly[( R )-hydroxybutyrate]. The key step depends on the ability to cleanly invert the stereochemistry of ( R )-ethyl 3-hydroxybutyrate via its mesylate ester under neutral conditions, avoiding the competing elimination process. This has been achieved in good (75%) yield on >100 g scale by controlled addition of the mesylate to a stirred slurry of calcium carbonate in water at 80 °C.