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Method for preparing S-1-aminoindane

A technology of aminoindane and raw materials, which is applied in the field of resolution and preparation of optical pure chiral compounds, and achieves the effects of cost reduction, good effect and simple resolution method

Inactive Publication Date: 2015-11-18
吴玲
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing reports on the resolution and preparation of 1-aminoindane, most of them are about how to prepare R-1-aminoindane, and there are few reports on how to prepare optical S-1-aminoindane

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] (1)

[0009] In a 1000ml round bottom flask, add 18.2G (0.12mol) D-mandelic acid to a mixed solution of methanol (200ml) and water (100ml), heat to 50°C, add 13.3G (0.1mol) of 1-aminoindane ), reflux reaction for 1.5 hours, cooled to room temperature, and filtered to obtain the crude product of D-mandelic acid salt of S-1-aminoindane. The obtained salt was added to a mixture of methanol (100 ml) and water (50 ml) for recrystallization to obtain 10.9 g of D-mandelic acid salt of S-1-aminoindane.

[0010] (2)

[0011] Dissolve 10.9 g of D-mandelate salt of S-1-aminoindane obtained in the previous step in 200 ml of water, add dropwise 40% sodium hydroxide solution to adjust the pH value to 12, and extract with dichloromethane (100 ml, 50 ml, 50 ml) 3 times, the dichloromethane layers were combined, washed once with water (50ml) and saturated brine (50ml), dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 4.5g of S-1-aminoindane with a yield of 34%...

Embodiment 2

[0015] (1)

[0016] In a 1000ml round bottom flask, add 22.8G (0.15mol) D-mandelic acid into a mixed solution of ethanol (200ml) and water (200ml), heat to 50°C, add 13.3G (0.1mol) of 1-aminoindane ), reflux reaction for 1.0 hour, cooled to room temperature, and filtered to obtain the crude product of D-mandelic acid salt of S-1-aminoindane. The resulting salt was added to a mixture of ethanol (110ml) and water (40ml) for recrystallization to obtain 9.8g of D-mandelic acid salt of S-1-aminoindane.

[0017] (2)

[0018] Dissolve 9.8 g of D-mandelate salt of S-1-aminoindane obtained in the previous step in 300 ml of water, add ammonia water dropwise to adjust the pH value to 13, extract 3 times with ethyl acetate (100 ml, 50 ml, 50 ml), dichloro The methane layers were combined, washed once with water (50ml) and saturated brine (50ml), dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 4.1g of S-1-aminoindane with a yield of 30.8% and an ee value of 99.4...

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PUM

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Abstract

The invention discloses a method for preparing S-1-aminoindane through separation. D-mandelic acid is taken as a chirality resolving agent, a mixed solution of alcohol and water is taken as a solvent, under the condition of heating reflux, 1-aminoindane is dropwise added and racemized, the 1-aminoindane is reacted with the D-mandelic acid to form diastereomeric salt, and the D-mandelate of the S-1-aminoindane is obtained through crystallization and separation according to different solubility of the diastereomeric salt; the S-1-aminoindane is obtained by conducting purification and alkalization on the D-mandelate; all the solutions containing the D-mandelate are mixed, the alcohol is removed through steaming, acidification is conducted on the solution, and the D-mandelate can be recycled. The method for preparing the S-1-aminoindane through the separation has the advantages of being mild in condition, easy to operate, high in product yield, high in optical purity, capable of recycling and reusing the resolving agent and the like, and the method is extremely suitable for industrial production of the S-1-aminoindane.

Description

technical field [0001] The invention relates to a method for the resolution and preparation of optically pure chiral compounds, in particular to a method for the resolution and preparation of S-1-aminoindane. Background technique [0002] S-1-Aminoindane and its hydrochloride are very important pharmaceutical intermediates. In the existing reports on the separation and preparation of 1-aminoindan, most of them are about how to prepare R-1-aminoindan, but there are few reports on how to prepare optical S-1-aminoindan. How to obtain an efficient and cheap chemical resolution method is the problem to be solved by the present invention. Contents of the invention [0003] The purpose of the present invention is to provide a low-cost and simple method for obtaining optically pure S-1-aminoindan by resolution. In the present invention, by using D-mandelic acid as a resolving agent, the resolution and preparation of S-1-aminoindane are successfully realized. The specific operat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/42C07C209/88
Inventor 吴玲
Owner 吴玲
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