Journal
TETRAHEDRON-ASYMMETRY
Volume 15, Issue 5, Pages 821-825Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2003.12.005
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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 degreesC. (C) 2003 Elsevier Ltd. All rights reserved.
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