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Stereospecific synthesis and optical resolution of 5-hydroxypipecolic acid

✍ Scribed by H. C. Beyerman; P. Boekee

Book ID: 104586081
Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 618 KB
Volume: 78
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19590780903

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✦ Synopsis

Abstract

The synthesis is described of 5‐hydroxypipecolic acid by reduction with sodium borohydride of the corresponding keto‐acid, which in turn was prepared from glutamic acid. This reduction proceeds without any appreciable formation of allo‐isomer.

The optical resolution is also described and the rotations of the optical antipodes are compared with those mentioned in the literature for the natural product.

Further evidence is given for the cis‐OH/COOH configuration of the DL‐allo‐acid.

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