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Synthesis method of levo-amino compound

A synthetic method and technology of L-amine group, which is applied in the field of preparation of optically pure L-chiral amine compounds, can solve problems such as not being seen, and achieve the effects of good product yield, easy availability of raw materials, and high purity

Inactive Publication Date: 2017-03-01
王际菊
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] In the existing relevant research, the existing reports about the method for preparing 7-chloro-1,2,3,4-tetrahydronaphthalene-1-amine are mainly raw material 7-chloro-1 tetralone in methanol solvent React with methoxylamine hydrochloride, further react with borane in tetrahydrofuran, and finally alkalinize with sodium hydroxide to obtain 7-chloro-1,2,3,4-tetrahydronaphthalene-1-amine ( Preparation of novel 2-aminobenzonzimidazole derivatives as modulators of small-conductancecalcium-activated potassium channels, PCT Int. Appl., 2006013210, 09 Feb2006); and how to resolve and prepare its optical purity S-7-chloro-1,2,3 , the report of 4-tetrahydronaphthalene-1-amine was not seen

Method used

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  • Synthesis method of levo-amino compound

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Embodiment 1

[0007] 1. Synthesis of 7-Chloro-1 Tetralone Oxime

[0008] In the three-necked flask, add 500ml of methanol as a solvent, add 90g of raw materials 7-chloro-1-tetralone, 38.2g of hydroxylamine hydrochloride, and dropwise add a concentration of 40% sodium hydroxide solution in batches under the condition of stirring at room temperature until the pH of the system is Weakly alkaline, continue to stir and react for 2 hours after adding, stop the reaction when the point of raw material 7-chloro-1 tetralone disappears by pointing the plate; under stirring conditions, add 2000ml of water to the system, and a large amount of white solids precipitate out; After suction filtration, the resulting filter cake was washed with water until it became neutral, and then dried for later use. In this step, 95.9 g of 7-chloro-1-tetralone oxime was obtained, with a yield of 98.4%.

[0009] 2) Reductive amination of 7-chloro-1 tetralone oxime

[0010] In the autoclave, add 600ml of anhydrous methano...

Embodiment 2

[0016] 1) Synthesis of 7-Chloro-1 Tetralone Oxime

[0017] In the three-necked flask, add 1000ml of methanol as a solvent, add 180g of raw materials 7-chloro-1-tetralone, 77g of hydroxylamine hydrochloride, and add a concentration of 40% sodium hydroxide solution in batches under the condition of stirring at room temperature until the pH of the system is weak. Alkaline, continue to stir and react for 2.5 hours after adding, stop the reaction when the point of raw material 7-chloro-1 tetralone disappears by pointing the plate; under stirring conditions, add 4000ml of water to the system, a large amount of white solids are precipitated; After filtering, the resulting filter cake was washed with water until neutral, and dried for later use. This step gave 193.2 g of 7-chloro-1 tetralone oxime, with a yield of 99.1%.

[0018] 2) Reductive amination of 7-chloro-1 tetralone oxime

[0019] In the autoclave, add 600ml of anhydrous methanol as a solvent, 193.2g of 7-chloro-1 tetralone...

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Abstract

The invention discloses a synthesis method of a levo-amino compound S-7-chloro-1,2,3,4-tetrahydronaphthalene-1-amine. The method includes the steps of: performing a reaction to a raw material, 7-chloro-1-tetralone, with hydroxylamine to generate oxime; performing hydrogenation reduction to the oxime to prepare racemized amine; performing a one-pot dynamic kinetic resolution reaction to the product amine with lipase, a racemization catalyst and an acyl group donor; and hydrolyzing a resolution reaction product to prepare the S-7-chloro-1,2,3,4-tetrahydronaphthalene-1-amine. The method has simple operations, high product yield, high optical purity of the resolution product, and the like.

Description

technical field [0001] The present invention relates to a method for preparing optically pure left-handed chiral amine compounds, in particular to a method for preparing S-7-chloro-1,2,3, 4-Tetralin-1-amine method. Background technique [0002] In the existing relevant research, the existing reports about the method for preparing 7-chloro-1,2,3,4-tetrahydronaphthalene-1-amine are mainly raw material 7-chloro-1 tetralone in methanol solvent React with methoxylamine hydrochloride, further react with borane in tetrahydrofuran, and finally alkalinize with sodium hydroxide to obtain 7-chloro-1,2,3,4-tetrahydronaphthalene-1-amine ( Preparation of novel 2-aminobenzonzimidazole derivatives as modulators of small-conductancecalcium-activated potassium channels, PCT Int. Appl., 2006013210, 09 Feb2006); and how to resolve and prepare its optical purity S-7-chloro-1,2,3 , The report of 4-tetrahydronaphthalene-1-amine could not be seen. Contents of the invention [0003] The present...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/08C07C251/44C07C209/40C07C209/62C07C211/42C12P13/02C12P41/00
CPCC07C249/08C07B2200/07C07C209/40C07C209/62C12P13/02C12P41/006C07C251/44C07C211/42
Inventor 王际菊
Owner 王际菊
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