Dimethyl 3-hydroxyglutarate

Chemical Properties

Off-White to Pale Yellow Oil

Uses

Dimethyl 3-hydroxyglutarate was used in the synthesis of two chiral fragments representing C1-11 and C12-25 of the polyene macrolide pimaricin.

Uses

Glutaric Acid derivative

General Description

Enantioselective hydrolysis and ammonolysis of dimethyl-3-hydroxyglutarate has been studied using immobilized lipase B isolated from Candida antarctica.

Synthesis

To a stirred solution of dimethyl 3-oxoglutarate (17.7 mL, 120.6 mmol) in methanol (315 mL) at 0 °C was added sodium borohydride (3.9 g, 102.5 mmol) in batches. After the reaction mixture was brought to room temperature, the reaction was continued with stirring for 24 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 5-6 by adding solid citric acid to quench the reaction. Subsequently, silica gel (about 1 g) was added to the reaction mixture and the solvent was removed by rotary evaporation. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1:1) to afford dimethyl 3-hydroxyglutarate (19.98 g, 94% yield) as a colorless oil.

References

[1] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 1, p. 172 - 175
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3650 - 3653
[3] Journal of Organic Chemistry, 1988, vol. 53, # 7, p. 1567 - 1569
[4] RSC Advances, 2016, vol. 6, # 27, p. 22737 - 22748
[5] Journal of the American Chemical Society, 2009, vol. 131, # 49, p. 17980 - 17985