Preparation of R-6-methoxy-1-aminoindane through resolution

An aminoindane, R-6- technology, which is applied in the field of separation and preparation of optically pure chiral compounds, can solve the problems of separation and preparation of R-6-methoxy-1-aminoindene, etc., and achieves complete utilization of raw materials. , cheap and easy to obtain optical purity, simple operation effect

Inactive Publication Date: 2015-11-18
陈永军
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It can be found through the research literature that there is no information on how

Method used

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Examples

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Effect test

Embodiment 1

[0007] 1. Resolution of 6-methoxy-1-aminoindan

[0008] In a 1000ML autoclave, add 500ML toluene, 81.6G6-methoxy-1-aminoindan, 115.9gD-(-)-O-acetylmandelic acid, 5g Candida plicata lipase and 10gKT-02, seal the high pressure In the autoclave, replace the air in the autoclave with nitrogen, then pass hydrogen into the autoclave to a pressure of 1.0MP, start stirring, and raise the temperature to 50°C for reaction; after 18 hours, take a sample for detection, 6-methoxy-1-amino Indane is completely converted into the acetyl compound of R-6-methoxy-1-aminoindane; after the reaction, the solution is concentrated and column chromatographed to obtain pure R-6-methoxy-1-aminoindane Full acetyl compound 97.5g, yield is 95.1%.

[0009] 2. Acid hydrolysis to obtain R-6-methoxy-1-aminoindan

[0010] Get 102.6g of the acetyl compound 102.6g of the R-6-methoxy-1-aminoindane that repeats several times to be made in the previous step and join in the solution that the ethanol of 1000ml and c...

Embodiment 2

[0014] 1. Resolution of 6-methoxy-1-aminoindan

[0015] In a 1000ML autoclave, sequentially add 500ML toluene, 81.6G6-methoxy-1-aminoindan, 144.9gD-(-)-O-acetylmandelic acid, 7g Candida plicata lipase and 12gKT-02, seal Autoclave, replace the air in the autoclave with nitrogen, then pass hydrogen into the autoclave to a pressure of 1.5MP, start stirring, and raise the temperature to 70°C for reaction; after 14 hours, sample detection, 6-methoxy-1 -Aminoindane is completely converted into an acetyl compound of R-6-methoxy-1-aminoindane; after the reaction, the solution is concentrated and column chromatography is obtained to obtain R-6-methoxy-1-amino The acetyl compound of indane was 97.1g, and the yield was 94.7%.

[0016] 2. Acid hydrolysis to obtain R-6-methoxy-1-aminoindan salt

[0017] Get 102.6 g of the acetyl compound of R-6-methoxy-1-aminoindane obtained by repeating the previous step several times and add it to the solution mixed with 1000 ml of ethanol and concentr...

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Abstract

The invention discloses a method for preparing R-6-methoxy-1-aminoindane through dynamic kinetic resolution. The method comprises the following steps: using 6-methoxy-1-aminoindane as a raw material, and under co-catalysis of a biological resolution catalyst, namely, candida rugosa lipase, and a racemization catalyst, namely, a non-crystal nickel catalyst KT-02, conducting transesterification reaction on 6-methoxy-1-aminoindane and an acyl donor, namely, (R)-(-)-alpha-acetylmandelic acid, to generate an R-6-methoxy-1-aminoindane acyl compound, and conducting acid hydrolysis and alkali ionization on the acyl compound to obtain R-6-methoxy-1-aminoindane, wherein the optical purity of the finished product is greater than 99%. The method has the characteristics that the operation is simple, the racemization catalyst is cheap and easy to obtain, the raw material utilization is complete, and the optical purity of the product is high. The method has great guidance and application values in preparation of R-6-methoxy-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 preparation of R-6-methoxyl-1-aminoindan by dynamic kinetic resolution. Background technique [0002] R-6-methoxy-1-aminoindan as a chiral intermediate. In the existing related research, there are few reports on how to prepare optically pure R-6-methoxy-1-aminoindan. It can be found through the research literature that there is no information on how to prepare R-6-methoxyl-1-aminoindan by kinetic and dynamic kinetic resolution. The present invention uses Candida plicate lipase as the resolution catalyst, KT-02 as the racemization catalyst, and successfully realizes dynamic kinetic resolution to prepare R- 6-methoxy-1-aminoindan, and the final product has good yield and high purity. Contents of the invention [0003] In order to solve the above problems, the present invention proposes dynamic kinetic resolution ...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P13/00
Inventor 陈永军
Owner 陈永军
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