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Enzymatic resolution method for preparation of (R)-1-(1-naphthyl) ethylamine

A technology of enzymatic separation and naphthyl, which is applied in the field of chemical enzymatic preparation of -1-ethylamine, can solve the problems of slow reaction speed of enzymatic method and easy falling off of palladium catalyst, and achieve high reusability and separation effect Excellent, good high temperature performance effect

Inactive Publication Date: 2019-01-18
JIANGSU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the problems that the palladium catalyst is easy to fall off and the reaction speed of the enzymatic method is slow, and improves the reuse rate of the palladium catalyst and the reaction rate of the separation of Candida Antarctica lipase B

Method used

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  • Enzymatic resolution method for preparation of (R)-1-(1-naphthyl) ethylamine
  • Enzymatic resolution method for preparation of (R)-1-(1-naphthyl) ethylamine
  • Enzymatic resolution method for preparation of (R)-1-(1-naphthyl) ethylamine

Examples

Experimental program
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Effect test

example 1

[0034] The method for preparing (R)-1-(1-naphthyl)ethylamine by chemical enzymatic dynamic kinetic resolution of the present embodiment has the following steps:

[0035] (1) Preparation of immobilized CALB: prepare 20ml of Candida antarctica lipase B enzyme solution with a concentration of 1.0mg / mL, hereinafter referred to as CALB, add 150mg of epoxy resin to the enzyme solution, stir at 25°C for 3h, and then The oxygen resin is separated from the enzyme solution, washed with a pH=7.0 buffer solution, and dried in vacuum to obtain immobilized CALB, and the weight percentage of the enzyme protein in the immobilized enzyme is 3.0%;

[0036] (2) Reaction system A: In 5 mL of toluene solvent, add 250 mg of immobilized CALB prepared in step (1), 2565 mg of 1-(1-naphthyl) ethylamine racemate, and 264 mg of ethyl ethoxyacetate Esters were reacted at a constant temperature of 50°C for 9 hours. After the reaction, the solid and liquid were separated, the immobilized CALB was left in th...

example 2～ example 5

[0041] The method of each example is basically the same as Example 1, and the differences are shown in Table 1.

[0042] Table 1

[0043]

[0044] It can be seen from Table 1 that under the same conditions, the carrier KCO 3 / Al 2 o 3 Immobilized nano-palladium works best as a racemization catalyst.

Embodiment 8～ Embodiment 14

[0046] Each embodiment is basically the same as embodiment 1 (that is, the immobilized nano-palladium of embodiment 1 is used), and the differences are shown in Table 2.

[0047] Table 2

[0048]

[0049] It can be seen from Table 2 that in the case of using the same immobilized enzyme, the chemical enzyme resolution effect of Example 12 (at a racemization temperature of 90° C. and a hydrogen pressure of 0.02 MPa) is the best.

[0050] The following control experiment adopts embodiment 12.

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Abstract

The invention provides a chemical enzymatic method for preparing (R)-1-(1-naphthyl) ethylamine, wherein the nano palladium is supported by a solid superbase to obtain immobilized palladium; Candida Antarctica lipase B (CALB) was covalently bound to the surface of epoxy resin carrier to obtain immobilized CALB. In reaction system A, immobilized CALB was used as catalyst, toluene as solvent, ethoxyacetate as acyl donor, (R)-1-(1-naphthyl) ethylamine is selectively esterified, solid-liquid separation is carried out after the reaction, immobilized CALB is left in the reaction system A, liquid phase is removed from the reaction system A into the reaction system B, and the palladium catalyst is immobilized by the method, so that the reuse rate of the palladium catalyst is increased.

Description

technical field [0001] The invention relates to a biological resolution method, in particular to a chemical and enzymatic preparation method of (R)-1-(1-naphthyl)ethylamine. Background technique [0002] (R)-1-(1-naphthyl)ethylamine is an important chiral block for preparation, and the current methods for the resolution and preparation of (R)-1-(1-naphthyl)ethylamine mainly include chemical and enzymatic methods : [0003] Chemical resolution method: L-aspartic acid (CN101407465A), chiral naproxen (such as international patent document WO2008058235A2), chiral tartaric acid (such as international patent document WO2004110976A2, Chinese patent document CN101735070A, Chinese patent document CN103420845A), etc. The chiral resolving agent forms a salt with 1-(1-naphthyl)ethylamine racemate, and the solubility of different chiral 1-(1-naphthyl)ethylamine salts in solvents is different, and the (S) -1-(1-naphthyl)ethylamine and (R)-1-(1-naphthyl)ethylamine were separated. The pr...

Claims

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Application Information

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IPC IPC(8): C12P41/00C12P13/00C12R1/72
CPCC12P13/001C12P41/00
Inventor 汪斌贡洁翁居轼杨凤丽陈舟梁国斌叶招莲刘维桥
Owner JIANGSU UNIV OF TECH
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