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Method for preparing (S)- 6-hydroxy-1-aminoindan

A technology of aminoindane and S-6-, which is applied in the field of separation and preparation of optical pure chiral compounds, to achieve the effects of high resolution efficiency, easy separation and recycling, and stable chemical properties

Inactive Publication Date: 2015-12-23
吴玲
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the existing reports on (R,S)-6-hydroxy-1-aminoindan, there are few reports on how to prepare optically pure S-6-hydroxy-1-aminoindan

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0008] (1) Resolution of (R,S)-6-hydroxy-1-aminoindan

[0009] In a 1000ml round bottom flask, add 22.8G (0.15mol) D-mandelic acid and 400ml methanol, stir magnetically, add 14.9G (0.1mol) (R,S)-6-hydroxy-1-aminoindene dropwise at 55°C Full, reflux reaction 1.5h. Naturally cooled, cooled to room temperature, a white precipitate was precipitated, and 13.4 g of a white product was obtained by suction filtration. Recrystallized with 130ml of methanol to obtain 12.1g of refined D-mandelate salt of S-6-hydroxy-1-aminoindan with a yield of 42.8%.

[0010] (2) Preparation of S-6-hydroxy-1-aminoindan

[0011] Dissolve 12.1 g of D-mandelate salt of S-6-hydroxy-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 dichloromethane (100 ml, 50 ml , 50ml) extracted 3 times, the dichloromethane layers were combined, washed once with water (50ml) and saturated brine (50ml), dried over anhydrous sodium s...

Embodiment 2

[0015] (1) Resolution of (R,S)-6-hydroxy-1-aminoindan

[0016] In a 1000ml round bottom flask, add 18.2G (0.12mol) D-mandelic acid and 300ml ethanol, stir magnetically, add 14.9G (0.1mol) (R,S)-6-hydroxy-1-aminoindene dropwise at 50°C Full, reflux reaction 2h. Naturally cooled, cooled to room temperature, a white precipitate was precipitated, and 14.1 g of a white product was obtained by suction filtration. Recrystallized with 140ml of methanol to obtain 12.9g of refined D-mandelate salt of S-6-hydroxy-1-aminoindan with a yield of 45.6%.

[0017] (2) Preparation of S-6-hydroxy-1-aminoindan

[0018] Dissolve 12.9g of D-mandelate salt of S-6-hydroxy-1-aminoindane obtained in the previous step in 200ml of water, add ammonia solution dropwise to adjust the pH value to 13, and extract with ethyl acetate (100ml, 50ml, 50ml) 3 times, the ethyl acetate layers were combined, washed once with water (50ml) and saturated brine (50ml), dried over anhydrous sodium sulfate, filtered, and ...

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Abstract

The invention discloses a method for preparing (S)- 6-hydroxy-1-aminoindan by utilizing a chiral resolving agent (R)-(-)-amygdalic acid to resolve (R,S)-6-hydroxy-1-aminoindan. The method comprises reacting (R)-(-)-amygdalic acid with resolve (R,S)-6-hydroxy-1-aminoindan in a solution to obtain a diastereomer salt of (S)- 6-hydroxy-1-aminoindan and (R)-(-)-amygdalic acid, and performing recrystallization and alkalization on the salt to obtain (S)- 6-hydroxy-1-aminoindan. Solutions containing (R)-(-)-amygdalic acid are merged, and the resolving agent (R)-(-)-amygdalic acid can be recovered after acidification. The provided method is simple in operation and high in resolving efficiency, the resolving agent and the resolving solvent are easy to recover for reusing, environment pollution is small, and the method is suitable for industrialized production.

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 preparing S-6-hydroxyl-1 by splitting (R,S)-6-hydroxyl-1-aminoindan with D-mandelic acid - The method of aminoindane. Background technique [0002] S-6-hydroxy-1-aminoindan is a very important class of chiral pharmaceutical intermediates. Among the existing reports on (R,S)-6-hydroxy-1-aminoindan, there are few reports on how to prepare optically pure S-6-hydroxy-1-aminoindan. The chemical resolution method is a kind of resolution method suitable for industrialized production. 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-6-hydroxyl-1-aminoindan by resolution. The present invention uses D-mandelic aci...

Claims

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Application Information

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IPC IPC(8): C07C215/64C07C213/10C07B57/00
Inventor 吴玲
Owner 吴玲
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