The isolation and identifiction of 5-Hydroxypiperidine-2-carboxylic Acid from Leucaena glauca Benth

Hegarty, M. P.

doi:10.1071/ch9570484

Cited by 15 publications

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Stereospecific synthesis and optical resolution of 5‐hydroxypipecolic acid

Beyerman

Boekee

1959

Recl. Trav. Chim. Pays‐Bas

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The synthesis is described of 5hydroxypipecolic acid by reduction with sodium borohydride of the corresponding Let-acid, which in turn was prepared from glutamic acid. This reduction proceeds without any appreciable formation of alfo-isomer.The optical resolution is also described and the rotations d the optical antipodes are compared with those mentioned in the literature for the natural product.Further evidence is given for the c i s -o M /~ configuration of the m.-alfo-add. 0 1. In our previous paper we gave -in addition to a sumrey about the occurrence in nature of 5-hydroxypipecolic acid -a description of the conversion of kojic acid into a mixture of DL-S-'hydroxypipecolic acid (X) and ~~-allo-5-hydroxypipecolic acid (IX) 1.W e stated that these racemates can be separated by fractional crystallization *; chramatographic separations on a small scale have been described by others 81 4. From the point of view of preparation none of these separation methods is satisfactory. It may be observed that this situation resembles that occurring with the synthesis of 4-hydroxyproline, where the metbods for the separation from the allo-compound are also cumbersome 5.In this paper we wish to present a stereospecific synthesis of DL-5-hydroxypipecolic acid ( X ) which makes a sepawtion from the diastereoisomeric pair unnecessary. The optical resolution is also dsscribed

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