A method for resolution and preparation of optically pure r-2-naphthylethylamine

A technology of R-2-, naphthylethylamine, which is applied in the field of separation and preparation of optically pure R-2-naphthaleneethylamine, can solve the problems of high optical purity, difficult products, difficult to obtain, etc., and achieves good yield, The effect of high optical purity

Active Publication Date: 2017-01-04
六安佳诺生化科技有限公司
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Problems solved by technology

[0003] Among the existing methods, asymmetric synthesis is costly and often difficult to obtain products with high optical purity; chemical resolution and enzymatic kinetic resolution have the disadvantage of low raw material utilization, which is only 50% at most; In the reported enzymatic dynamic kinetic resolution method, the racemization catalysts used are usually complexes of some noble metals such as ruthenium and rhodium. These racemization catalysts are extremely expensive, and when these racemization catalysts are used in the resolution preparation process , although a high conversion rate is achieved, it is difficult to obtain a high optical purity of the product

Method used

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  • A method for resolution and preparation of optically pure r-2-naphthylethylamine

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Embodiment Construction

[0008] 1) Resolution and preparation of (R)-(1-(2-naphthyl)ethyl)acetamide

[0009] Add 500mL of toluene to a 1000mL autoclave as a solvent, add 85.5g of 2-naphthylethylamine, 90.2g of R-1-phenylethyl alcohol acetate, 5g of lipase novozym 435 and 8g of Raney nickel in turn, and seal the autoclave after the addition Finally, the air in the autoclave was replaced with nitrogen, and then hydrogen gas was introduced into the autoclave to a pressure of 1.0MP, stirring was started, and the temperature was raised to 60°C for reaction; after 20 hours, sampling was performed, and 2-naphthylethylamine disappeared and completely converted to (R)-(1-(2-naphthyl)ethyl)acetamide, and the ee value of the product reaches 99%; The mixed solvent was subjected to column chromatography to obtain 102.3 g of pure (R)-(1-(2-naphthyl)ethyl)acetamide with a yield of 96%.

[0010] 2) Acid hydrolysis to obtain R-2-naphthylethylamine salt

[0011] Add 53 g of (R)-(1-(2-naphthyl) ethyl) acetamide prepar...

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Abstract

The invention relates to a method for preparing R-2-naphthylethylamine by dynamic kinetic resolution. Using 2-naphthylethylamine as raw material, Novozym 435 as a resolution catalyst, R-1-phenylethyl alcohol acetate as an acyl donor, and Raney nickel as a racemization catalyst, hydrogen is introduced into the autoclave to react, 2- Complete conversion of naphthylethylamine to obtain (R)-(1-(2-naphthyl)ethyl)acetamide (ee value 99%); acid hydrolysis after purification of the amide to obtain R-2-naphthylethylamine salt, which is passed through Operations such as alkalization, extraction, drying, and concentration can obtain R-2-naphthylethylamine, and the product yield and ee value of the whole steps can reach more than 90%. The invention has the characteristics of cheap and easy to obtain racemic catalyst, complete utilization of raw materials, good product yield, high optical purity and the like. In the production and preparation of R-2-naphthylethylamine, it has great guidance and application value.

Description

technical field [0001] The invention relates to a resolution and preparation method of optically pure chiral amine, in particular to a resolution and preparation method of optically pure R-2-naphthylethylamine. Background technique [0002] Optically pure chiral amines are very important pharmaceutical intermediates. At present, optically pure chiral amines are mainly obtained through the following methods: enzymatic resolution (Indian J. Chem. Sect. B 2005, 44, 1312-1316; J. Org. Chem. 1997, 62, 3488-3495); Chemical resolution: resolution with chiral α-hydroxyphenylacetic acid (US6342636; Tetrahedron: asymmetry, 1998, 9, 2219-2212) or protected chiral glycerol derivatives (Tetrahedron: asymmetry, 1996, 7, 1117-1122 ; Tetrahedron: asymmetry, 2002, 13, 2277-2282); obtained by asymmetric synthesis of the corresponding aldehyde (WO2004 / 110976; J. Org. Chem. 1992, 57, 1237-1241). [0003] Among the existing methods, the cost of asymmetric synthesis is high and it is often diff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P41/00C12P13/00C07C209/00C07C211/30
Inventor 陈永军
Owner 六安佳诺生化科技有限公司
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