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A method for enzymatic resolution and preparation of (s)-1-(1-naphthyl)ethylamine

A technology of enzymatic splitting and naphthyl, which is applied in fermentation and other directions, can solve the problems of slow reaction speed of enzymatic method, and achieve the effect of simple process, good high temperature resistance and high splitting efficiency

Inactive Publication Date: 2020-01-03
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 of slow reaction speed of the current enzymatic method, and improves the reaction rate of Candida Antarctica lipase B resolution

Method used

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  • A method for enzymatic resolution and preparation of (s)-1-(1-naphthyl)ethylamine
  • A method for enzymatic resolution and preparation of (s)-1-(1-naphthyl)ethylamine
  • A method for enzymatic resolution and preparation of (s)-1-(1-naphthyl)ethylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A method for enzymatic resolution and preparation of (S)-1-(1-naphthyl)ethylamine has the following steps:

[0026] ① First, prepare 50 mL of Candida antarctica lipase B (hereinafter referred to as CLAB) enzyme solution with a concentration of 1.0 mg / mL, add 150 mg of macroporous resin D3520 to the enzyme solution, stir at 25°C for 3 hours, and remove the resin from the enzyme solution Second, add CLAB-adsorbed resin to 50 mL of 0.5% glutaraldehyde solution, stir and cross-link at 25°C for 2 hours, finally, separate the resin from the glutaraldehyde solution, and wash with pH=7.0 buffer, Immobilized CLAB was obtained after vacuum drying.

[0027] ②In 5mL of toluene solvent, add 5mg of immobilized CLAB prepared in step ①, 2775mg of 1-(1-naphthyl)acetoxime racemate (1.5mmol, hereinafter referred to as racemate) and 264mg of Ethyl acetate (3.0 mmol), 1 g of CuY, and a hydrogen pressure of 0.1 MPa were reacted at a constant temperature of 80° C. for 18 h.

[0028] ③ After...

example 2～ example 5

[0032] The method of each example is basically the same as Example 1, and the differences are shown in Table 1.

[0033] Table 1

[0034] Adsorbent (S)-1-(1-naphthyl)ethylamine Example 1 D3520 2092mg, 82%, e.e.99.1% Example 2 H103 2017mg, 79%, e.e.98.7% Example 3 D151 2271mg, 89%, e.e.99.3% Example 4 D113 1827mg, 71%, e.e.99.1% Example 5 D301 1671mg, 65%, e.e.99.1%

[0035] As can be seen from Table 1, under other conditions being the same, the immobilized CLAB using adsorbent D151 (Example 3) is the best enzyme catalyst.

Embodiment 6～ Embodiment 17

[0037] Each example is basically the same as Example 3 (that is, the immobilized CLAB of Example 3 is used), and the differences are shown in Table 2.

[0038] Table 2

[0039] temperature racemic catalyst hydrogen pressure (S)1-(1-naphthyl)ethylamine Example 6 80℃ Pb / C 0.1MPa 2173mg, 86%, e.e.99.2% Example 7 80℃ Raney Nickel 0.1MPa 2107mg, 82%, e.e.99.1% Example 8 80℃ Ni / Al 2 o 3

[0040] As can be seen from Table 2, under the situation of adopting the same immobilized enzyme, embodiment 9 (under the temperature of 80 ℃, CuY is racemization catalyst and hydrogen pressure is 0.3MPa) and embodiment 10 resolution effect are the best . But the hydrogen pressure of embodiment 10 is greater than embodiment 9, and following control experiment adopts embodiment 9.

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Abstract

The invention relates to a method for preparing (S)-1-(1-naphthyl)ethylamine by an enzyme method. According to the method, Candida antarctica lipase B is adsorbed by macroporous resin, and cross-linking is carried out by using glutaraldehyde so as to obtain immobilized Candida antarctica lipase B. The immobilized lipase serves as a catalyst, toluene serves as a solvent, ethyl acetate serves as an acyl donor, (S)-1-(1-naphthyl)ethylketoxime is selectively esterified, (R)-1-(1-naphthyl)ethylamine is not esterified, and a racemation reaction is carried out in the presence of a racemation catalyst and hydrogen gas. According to the method, the immobilized Candida antarctica lipase B can be used for completely converting 1-(1-naphthyl)ethylketoxime into (S)-1-(1-naphthyl)ethylamine ethyl ester at a relatively high temperature, and the reaction has the characteristics of short reaction time, high product optical purity, and the like.

Description

technical field [0001] The invention relates to a biological resolution method, in particular to an immobilized enzyme resolution preparation method of (S)-1-(1-naphthyl)ethylamine. Background technique [0002] (S)-1-(1-naphthyl) ethylamine is a kind of important chiral medicine intermediate, the method for preparing (S)-1-(1-naphthyl) ethylamine mainly comprises following several classes at present (with raw material classification): [0003] (1) Asymmetric synthesis of 1-(1-naphthyl)ethanone: as shown in the following formula, 1-(1-naphthyl)ethanone is first catalytically hydrogenated to (R)-α- Naphthalene ethanol, and then reduced to obtain (S)-α-naphthylethylamine (such as international patent document WO2004110976A2). The chiral rhodium catalyst used in this method has a complex structure, is difficult to prepare, and has high cost, so it is difficult to industrialize large-scale production. [0004] [0005] (2) 1-(1-naphthyl)ethylamine chemical resolution metho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P41/00C12P13/00
CPCC12P13/001C12P41/00
Inventor 汪斌贺沁婷梁国斌姚鹏飞刘维桥翁居轼
Owner JIANGSU UNIV OF TECH
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