Synthetic method of (-)-Corey lactone diol

A technology of coreylactone diol and a synthetic method, which is applied in the synthetic field of coreylactonediol (Coreylactonediol), can solve problems such as inability to carry out large-scale production, instability of dichloride compounds, high price of alkaloids, etc. Achieve the effects of high resolution efficiency, short reaction time, and avoiding isomers

Inactive Publication Date: 2019-05-17
SHANGHAI MAOSHENG KAIHUI TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In this synthetic method, the dichloro compound is unstable and cannot be produced on a large scale
[0010] There are organic alkaloids such as quinine, strychnine, and ephedrine as chiral resolving agents for γ-lactones, but these alkaloids are expensive and difficult to popularize and use

Method used

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  • Synthetic method of (-)-Corey lactone diol
  • Synthetic method of (-)-Corey lactone diol
  • Synthetic method of (-)-Corey lactone diol

Examples

Experimental program
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Effect test

Embodiment 1

[0065] The synthesis of embodiment 1, compound 2

[0066] Add 200g of dicyclopentadiene into a 500ml eggplant-shaped bottle, heat it under stirring until it is completely dissolved and clarified, carry out rectification with a rectification column, and collect fractions at 38-42°C to obtain 192g of compound 2 (1,3-cyclopentadiene ene), yield 96%.

Embodiment 2

[0067] The synthesis of embodiment 2, compound 3

[0068] Add 100g of dichloroacetyl chloride, 103g of compound 2 (1,3-cyclopentadiene) and 0.68L of n-heptane into a 2L four-necked flask, and slowly drop triethylamine (72.4g) into n-hexane Alkane solution, dropwise, stirred overnight at room temperature. The filter residue was suction filtered, the filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure at low temperature, the residue was distilled under reduced pressure, and fractions at 50-54°C were collected to obtain 104 g of compound 3 with a yield of 86%.

[0069] 1 H NMR(500MHz,CHLOROFORM-d)ppm2.58(m,1H,CH),2.82(m,1H,CH),4.07(m,1H,CH),4.27(m,1H,CH),6.05(m ,1H,CH).

Embodiment 3

[0070] The synthesis of embodiment 3, compound 4

[0071] Add 100g of compound 3, 150ml of methanol, and 150ml of water into a 1L three-necked flask, place it in an ice-salt bath under stirring, and slowly add 110ml of 30% hydrogen peroxide dropwise at a controlled internal temperature of -5°C. After the drop is complete, slowly add 5N hydroxide Sodium aqueous solution, control the internal temperature not higher than 30°C, after dropping, stir overnight at room temperature.

[0072] Add sodium sulfite to quench excess hydrogen peroxide, after full reaction, add hydrochloric acid to adjust the acidity, filter out the salt in the system, extract with ethyl acetate, wash the organic phase with saturated brine, dry with anhydrous sodium sulfate, distill off the solvent under reduced pressure, and the residue Dissolve in methanol for clarification, then add n-pentane for crystallization, wash thoroughly, and filter out the solid with suction to obtain 479 g of white compound 4 wit...

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Abstract

The invention discloses a synthetic method of (-)-Corey lactone diol. According to the synthetic method, the target product is prepared from dicyclopentadiene as a raw material by depolymerization, cyclization, oxidation, dechlorination, ring opening, resolution, Prins reaction and hydrolysis reaction. The disclosed synthetic route adopts economical raw material and is high in resolution efficiency and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, relates to the chemical synthesis process of the key intermediate of prostaglandin medicine, in particular to a synthetic method of (-)-Corey lactone diol. Background technique [0002] Corylidene diol is a key intermediate in the synthesis of prostaglandin drugs. Prostaglandins (abbreviated as: PGs) are an important class of endogenous natural products with multiple biological activities; prostaglandins are a family of five The 20-carbon unsaturated hydroxy fatty acid with a member ring, whose parent is prostanoic acid, has certain effects on the respiratory system, gastrointestinal tract, cardiovascular system and platelet aggregation; it also has anti-disease, hypnotic, anti-inflammatory and anti-inflammatory properties. tumor activity. As a natural endogenous product, PGs are relatively less toxic to the human body, and can exert various physiological effects in a trace amou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/935
Inventor 应永铖易滔姜雪峰王甜甜俞斐
Owner SHANGHAI MAOSHENG KAIHUI TECH CO LTD
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