Nature

(s)-3-Hydroxy-γbutyrolactone is a colorless liquid, soluble in water, alcohol and other organic solvents, but insoluble in petroleum ether, etc. It is a very important organic synthesis intermediate and is also very important. Chiral Pool.

Use

Mainly used as a key intermediate of the regulator (R)-γ-hydroxy-β-Q-hydroxybutyric acid [(R)-GABOB]. (R)-GABOB is used to treat hyperlipidemia; (s)-Oxiracetam is a brain metabolism accelerator, and its synthesis; (s)-3-hydroxytetrahydrofuran can be obtained by reducing it, which is an important intermediate for AIDS treatment drugs; (s)-3-hydroxy-4- Bromobutyric acid is a potential stabilizer; converting it into (s)-5-hydroxymethyl-1,3-oxazolin-2-one can obtain the latest generation of antibacterial drugs; in addition, (s)-N- Methyl-3-hydroxypyrrole and (R)-N-methyl-3-methanopyrrole also have important physiological activities, and (s)-3-hydroxy-γbutyrolactone can also be produced through simple conversion And get. Many natural products can also be synthesized from (s)-3-hydroxy-γbutyrolactone.

Preparation

The preparation method of (S)-3-hydroxy-γ-butyrolactone relates to a chiral drug intermediate and provides (S)-3-hydroxy-γ-butyrolactone with cheap raw materials, simple process and high yield. (4) synthesis method. Dissolve (2R, 3R)-2,3-dihydroxy-γ-butyrolactone (1) in dichloromethane, cool to 0°C, add organic base acid binding agent dropwise, add sulfonylation reagent, and filter to remove the solid , after the solvent is evaporated, (2R, 3R)-2-sulfonyloxy-3-hydroxy-γ-butyrolactone (2) is obtained; (2R, 3R)-2-sulfonyloxy-3-hydroxy- Dissolve γ-butyrolactone (2) in an organic solvent, add an alkali metal halide, evaporate the solvent, add ethyl acetate for extraction, and evaporate the solvent under reduced pressure to obtain (2S, 3R)-2-halo-3-hydroxy. -γ-butyrolactone (3); Dissolve (2S, 3R)-2-halo-3-hydroxy-γ-butyrolactone (3) in an organic solvent, add a dehalogenation catalyst, filter out the solid and reduce the The solvent is evaporated under pressure, and the product is purified by column chromatography or distillation under reduced pressure.