5-hydroxypipecolic acid Chemical Properties

Melting point:

240-246 °C

Boiling point:

354.8±42.0 °C(Predicted)

Density 

1.299±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.31±0.40(Predicted)

5-hydroxypipecolic acid Usage And Synthesis

Definition

ChEBI: A piperidinemonocarboxylic acid that is pipecolic acid with a hydroxy substituent at position 5.

Synthesis

The general procedure for the synthesis of 5-hydroxypiperidine-2-carboxylic acid from 5-hydroxypyridine-2-carboxylic acid was as follows: compound XII (350.00 g, 2.516 mmol, 1.0 eq.) was dissolved in a solvent mixture of water (5 L) and methanol (1 L), and Pd(OH)2/C catalyst (50.00 g) was added. The mixture was transferred to an autoclave, charged with hydrogen to a pressure of 3.5 MPa, and reacted at 65°C for 24 hours. The reaction progress was monitored by LC-MS and stopped after confirming the complete disappearance of the feedstock. The reaction mixture was filtered to remove the catalyst and the filtrate was concentrated several times with toluene to give a product in the form of a brown liquid (365.22 g, aqueous solution), which was used directly in the next step of the reaction in a yield of 100% based on theoretical values.

References

[1] Patent: CN106045999, 2016, A. Location in patent: Paragraph 0068; 0069; 0070
[2] Recueil des Travaux Chimiques des Pays-Bas, 1958, vol. 77, p. 249,253

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