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

A technology of R-2- and naphthylethylamine, which is applied in the field of resolution and preparation of optically pure R-2-naphthylethylamine, can solve the problems of high optical purity, difficult products, and high cost of asymmetric synthesis methods, and achieves high yields. The effect of high efficiency and high optical purity

Active Publication Date: 2017-01-04
陈永军
View PDF5 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A method for resolution and preparation of optically pure r-2-naphthylethylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

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

[0009] 500mL of toluene was added to a 1000mL autoclave as a solvent, followed by 85.5g of 2-naphthylethylamine, 90.2g of D-(-)-O-acetylmandelic acid, 5g of lipase novozym 435 and 8g of KT-02 (nickel catalyst ), after the addition is complete, seal the autoclave and replace the air in the autoclave with nitrogen, then inject hydrogen into the autoclave to a pressure of 1.0MP, start stirring, and raise the temperature to 60°C for reaction; after 20 hours, take a sample for detection, The disappearance of 2-naphthylethylamine is completely converted into (R)-(1-(2-naphthyl) ethyl) acetamide, and the product ee value reaches 99%; after the reaction finishes, the solution is concentrated, and then the volume ratio is A 10:1 mixed solvent of n-hexane and ethanol 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 hydroly...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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 resolution catalyst, D‑(‑)‑O‑acetylmandelic acid as acyl donor, KT‑02 (nickel catalyst) as racemization catalyst, in autoclave 2-Naphthylethylamine is completely converted to obtain (R)-(1-(2-naphthyl)ethyl)acetamide (ee value 99%); acidolysis is carried out after amide purification to obtain R-2 ‑Naphthylethylamine salt, the salt is then basified, extracted, dried, concentrated, etc. to obtain R‑2‑naphthylethylamine. The product yield of each step can reach more than 90%, and the ee value is greater than 99%. 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(China)
IPC IPC(8): C12P41/00C12P13/00C07C209/00C07C211/30
Inventor 陈永军
Owner 陈永军
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap