Uses
(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid is a useful chemical intermediate for manufacturing of the anticonvulsant drug, Pregabalin
1, 2.
Sources
- https://quod.lib.umich.edu/a/ark/5550190.0011.a22?rgn=main;view=fulltext
- https://www.researchgate.net/publication/269660675_Synthesis_and_characterization_of_impurities_of_an_anticonvulsant_drug_Pregabalin
Chemical Properties
White Solid
Uses
An Impurity of the anti-convulsant (S)-Pregabalin (P704790).
Synthesis
The general procedure for the synthesis of (R)-(-)-3-(aminocarbonylmethyl)-5-methylhexanoic acid from the compound (CAS:1385049-51-3) is as follows:
Example 10f1: Synthesis of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid
1. ammonia (116 ml) was added to the diastereomeric salt (14.5 g) and the mixture was heated to 80 °C at room temperature.
2. After maintaining the reaction at this temperature for 5 hours, the reaction mixture was cooled to room temperature.
3. The reaction mixture was extracted using dichloromethane (5 x 50 ml).
4. The aqueous layer was cooled to 0 °C and acidified to pH 1 with concentrated hydrochloric acid.
5. The acidified aqueous layer was extracted using hot ethyl acetate (5 x 50 ml).
6. All organic extracts were combined and concentrated under reduced pressure to give enantiomerically enriched amide I as a white solid.
Yield: 8 g, 53% yield; HPLC purity: 99.39%.
References
[1] Patent: WO2012/93411, 2012, A2. Location in patent: Page/Page column 23
