Method for preparing optical activity 3-hydroxycarboxylate

A hydroxycarboxylate, optically active technology, applied in the field of preparation of optically active 3-hydroxycarboxylate, can solve the problems of expensive, no large-scale production, toxic phosphine ligands, etc., and achieves equipment requirements and reaction conditions. , The effect of equipment requirements is easy

Inactive Publication Date: 2008-03-19
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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-ketoe...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Into a 35ml autoclave, add 4.0mL methanol, 1.0mL (14.3mmol, >80%ee) (S)-propylene oxide, 0.125mmol (43mg) dicobalt octacarbonyl, 0.25mmol (17mg) Pyrazole, closed reactor. The reaction system was purged with carbon monoxide gas, filled with CO gas at a pressure of 6.0 MPa, and reacted at 80°C for 6 hours. The reaction vessel was cooled to room temperature, the remaining gas was vented, the reaction solution was taken out, and the reaction liquid was taken out. The conversion rate of (S)-propylene oxide was 96%, and the selectivity of (S)-3-hydroxybutyrate methyl ester was 94%. S) The enantioselectivity of methyl-3-hydroxybutyrate is 77%.

Embodiment 2

[0030] Same as Example 1, the co-catalyst used is imidazole, the conversion rate of (S)-propylene oxide is 68%, the selectivity of (S)-3-hydroxybutyrate is 95%, and the selectivity of (S)-3-hydroxybutyrate is 95%. The methyl ester enantioselectivity is 77%.

Embodiment 3

[0032] Same as Example 1, the co-catalyst used is 3-hydroxypyridine, the conversion rate of (S)-propylene oxide is 80%, the selectivity of (S)-3-hydroxybutyrate is 95%, (S)-3- The enantioselectivity of methyl hydroxybutyrate is 75%.

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PUM

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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...

Claims

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Application Information

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IPC IPC(8): C07C69/675C07C67/36
Inventor 陈静刘建华夏春谷童进
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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