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S-4- methyloctane derivate, synthetic method thereof and application thereof to (S)-3-methyl-heptanoate sythesis

A technology of methyl octane and synthesis method, applied in the directions of organic chemistry methods, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as complicated methods, and achieve the effects of simple operation and high efficiency

Inactive Publication Date: 2008-10-01
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of reaction is more complicated due to the use of chiral prosthetic groups

Method used

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  • S-4- methyloctane derivate, synthetic method thereof and application thereof to (S)-3-methyl-heptanoate sythesis
  • S-4- methyloctane derivate, synthetic method thereof and application thereof to (S)-3-methyl-heptanoate sythesis
  • S-4- methyloctane derivate, synthetic method thereof and application thereof to (S)-3-methyl-heptanoate sythesis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 compound 2a

[0029]

[0030] Take a 50mL bottle, weigh metal magnesium (0.632g, 26mmol) in it, add 20mL of freshly distilled tetrahydrofuran under the protection of argon, and then add dropwise a solution containing n-propyl bromide (2.2mL, 24mmol, 2.4eq.) under reflux. 20mL of freshly steamed tetrahydrofuran solution, after the dropwise addition, continue to stir for 1h;

[0031] Take a 250mL three-neck flask, vacuumize and fill it with argon three times, add anhydrous tetrahydrofuran 25ml, compound 5a (2.03g, 10mmol, 1eq.), N-methyl-2-pyrrolidone ( NMP) (3.6ml, 20.9mmol, 4eq.), and Li 2 CuCl 4 solution in THF (0.6 mL, 1.5 mol / L, 1 mmol). Add the Grignard reagent of n-propylmagnesium bromide into the constant-pressure dropping funnel, slowly drop it into the system at room temperature, and react at room temperature for about 4 hours after the addition, add saturated ammonium chloride solution to the reaction solut...

Embodiment 2

[0032] The synthesis of embodiment 2 compound 2b

[0033]

[0034]Take a 50mL bottle, weigh metal magnesium (0.632g, 26mmol) in it, add 20mL of freshly distilled tetrahydrofuran under the protection of argon, and then add dropwise a solution containing n-propyl bromide (2.2mL, 24mmol, 2.4eq.) under reflux. 20mL of freshly steamed tetrahydrofuran solution, after the dropwise addition, continue to stir for 1h;

[0035] Take a 250mL three-neck flask, vacuumize and fill it with argon three times, add anhydrous tetrahydrofuran 25ml, compound 5b (2.71g, 10mmol, 1eq.), N-methyl-2-pyrrolidone ( NMP) (3.6ml, 20.9mmol, 4eq.), and Li 2 CuCl 4 solution in THF (1 mL, 1.5 mol / L, 1.5 mmol). Add the Grignard reagent of n-propylmagnesium bromide into the constant pressure dropping funnel, slowly drop it into the system at room temperature, after the dropwise addition, react at room temperature for about 7 hours, add saturated ammonium chloride solution to the reaction so...

Embodiment 3

[0036] The synthesis of embodiment 3 compound 3

[0037]

[0038] Take a 100mL bottle, weigh metal magnesium (0.322g, 13.4mmol) into it, add 15mL of freshly distilled tetrahydrofuran under the protection of argon, and then add dropwise 5mL of freshly distilled tetrahydrofuran containing bromobenzene (1.4mL, 13.3mmol, 2.3eq.) The tetrahydrofuran solution, continue to stir for 0.5h after the dropwise addition. Add compound 2a (0.99g, 5.76mmol, 1eq.) 10mL freshly steamed tetrahydrofuran solution dropwise, react at room temperature for 6h, add 1.2M hydrochloric acid to quench the reaction, and then separate the liquids, extract the aqueous phase with ethyl acetate three times, combine the organic phases, Wash once with saturated sodium bicarbonate, once with saturated brine, dry over anhydrous sodium sulfate, filter, spin off the solvent under reduced pressure, and obtain 1.426 g of compound 3 with a yield of 84% by silica gel column chromatography. [α] D ...

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Abstract

The invention relates to an (S)-4-methyloctane compound and a synthesis method thereof. The compound can be used for the synthesis of optically pure (S)-3-methylheptanoic acid. The structural formula of the (S)-4-methyloctane compound is the formula and compared with the existing methods, the method for the synthesis of the optically pure (S)-3-methylheptanoic acid by utilizing the invention is easier and more convenient to operate, efficient and conducive to the utilization of steroidal sapogenins oxidative degraded waste.

Description

technical field [0001] The invention relates to a class of (S)-4-methyloctane derivatives, which can be conveniently prepared from small segment lactones obtained by the degradation of steroidal sapogenins, and these compounds can be used to synthesize optically pure (S) )-3-methylheptanoic acid. Utilizing the method described in the present invention to synthesize (S)-3-methylheptanoic acid is easier and more efficient than existing literature. technical background [0002] Optically active 3-methylheptanoic acid is an important chiral intermediate in organic synthesis, and (S)-3-methylheptanoic acid (1) is a raw material for the synthesis of cycloprostaglandin ISM10902 and prostaglandin E1 analogues. Therefore, the synthesis of (S)-3-methylheptanoic acid has attracted the attention of chemists. [0003] [0004] Cycloprostaglandin ISM10902 Prostaglandin E1 analog [0005] In 1978, the Teruaki Mukaiyama group of the University of Tokyo developed a method based on a ch...

Claims

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Application Information

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IPC IPC(8): C07C69/24C07C33/24C07C15/16C07C51/25C07C51/34C07C53/126C07B49/00
Inventor 田伟生张顺吉汪昀
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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