Uses
Cis-4-Hydroxycyclohexanecarboxylic acid is a metabolite of p-hydroxybenzoic acid. It is the major metabolite in the urine of rats treated with exogenous p-hydroxybenzoic acid. It has been found to have immunosuppressive activities in rat hepatocytes, as well as metabolic disorders that are related to hyperglycemia or diabetes mellitus.
Synthesis
cis-4-Hydroxycyclohexanecarboxylic acid can be synthesized through the following steps:
1. In an argon glove box, dissolve ligands L1-(S,R)-f-ambinol (7.5mg, 0.0105mmol) and [Ir(COD)Cl]2 (3.4mg, 0.005mmol) in 1 mL of iPrOH in a 2mL vial and stir at room temperature for 2 h.
2. Put 1 mmol of raw material 4-substituted cyclohexanone into a 4 mL hydrogenation flask.
3. Add 0.1 mL of the in-situ complexed catalyst solution and 1.6 mg of tBuOLi solid powder to the hydrogenation flask.
4. Add 1 mL of EtOH to dissolve the reactants in the hydrogenation flask.
5. Put the reaction flask into the hydrogenation kettle and replace the kettle body with hydrogen three times.
6. Fill the kettle with 5bar H2 and react at room temperature for 12h.
7. After the reaction is completed, carefully release the hydrogen and spin-dry the solvent under reduced pressure.
8. Purify the hydrogenated product cis-4-substituted cyclohexanol by silica gel column.
9. Obtain the final product cis-4-Hydroxycyclohexanecarboxylic acid.
