Method for preparing optical activity 3-hydroxycarboxylate

Abstract

The invention discloses a method in which carbonylation reaction is carried out between an epoxy compound and carbon monoxide and alcohol in order to prepare optically active 3-hydroxy carboxylic ester. The method uses the chiral epoxy compound, the monohydric alcohol and the carbon monoxide as reactants, cobalt carbonyl as main reactive catalyzer and a heterocyclic compound containing nitrogen as cocatalyst to synthesize the optically active 3-hydroxy carboxylic ester under the controlled operational conditions of reaction pressure between 3.0 MPa and 10.0 MPa, reaction temperature between 50 DEG C and 150 DEG C and reaction time between 1 and 8 hours. Under the relatively mild conditions, the invention can realize high conversion rate of chiral epoxy dimethylmethane and high selectivity of 3-hydroxy carboxylic ester, and therefore the invention is a high-efficiency, economical, environment-friendly and conveniently operated catalyzer system.

Description

Technical field [0001] The present invention relates to a method for preparing optically active 3-hydroxy carboxylic acid ester. Specifically, the present invention relates to a method for preparing optically active 3-hydroxy carboxylic acid ester by carbonylation reaction of epoxy compound, carbon monoxide and alcohol. Background technique [0002] Optically active 3-hydroxy carboxylic acid ester is a kind of pharmaceutical and organic intermediates with a wide range of uses. It is widely used in the pharmaceutical industry, agricultural chemistry, polyester industry, cosmetics industry, food additive industry and other important chiral fine compounds. synthesis. [0003] Take S-type 3-hydroxybutyrate as an example: 1) It can undergo a reduction reaction to obtain (S)-1,3-butanediol, an important intermediate widely used in the synthesis of antibiotics and pheromone. 2) With S-type 3-hydroxybutyrate as the starting material, S-lavender alcohol, S-citronellol, etc., which are wid...

AI Technical Summary

Problems solved by technology

But, there are many problems in this method equally: chemical method reduction β-ketoester needs expensive noble metal catalyst, complicated, expensive, poisonous phosphine ligand, needs high pressure hydrogen simultaneously, relatively high to the requirement of equipment (R.Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc. 1987, 109, 5856; M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, R. Noyori, J. Am. Chem. Soc. 1988, 110, 629); The cost of biological reduction of β-ketoesters in the presence of enzymes High, low catalytic efficiency (T.Johanson, M.Katz, M.F.Gorwa-Grauslund, FEMS Yeast Research2005, 5, 513; D.S.Pereira, R.Crit.Rev.Biotechnol.1998, 18, 25; J.D.Stewart, Current Opinion in Drug Discovery & Development 1998, 1, 278.)

However, the obtained results are not ideal, and there are still defects such as the conversion rate of the substrate, the selective yield of the target product, and the low catalytic efficiency, and it needs to be completed under high pressure (P(CO)>14.0MPa) and high temperature, so No prospects for mass production