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Prepn of (S)-(+)-2-amino propanol

A technology of aminopropanol and methylaziridine, which is applied in the field of preparation of 2-aminopropanol, can solve the problems of high cost of levofloxacin and high cost of raw materials, achieve good industrial application prospects and reduce production costs. Effect

Inactive Publication Date: 2008-11-26
SHANGHAI KELY BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the raw material cost of preparing (S)-(+)-2-aminopropanol is as high as more than 300,000 yuan / ton, which makes the cost of levofloxacin high.

Method used

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  • Prepn of (S)-(+)-2-amino propanol

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Experimental program
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Effect test

Embodiment 1

[0020] (1) Put 100g of (S)-propylene oxide, 300g of liquid ammonia, and 3g of p-toluenesulfonic acid in a reaction vessel at low temperature, stir after sealing, and slowly heat up. As the temperature rises, the liquid ammonia vaporizes, and the pressure in the container gradually increases. When the pressure gauge shows that it reaches 3.5MPa, the temperature reaches 70-80°C. Heat preservation and pressure, and react for 30 hours. Gradually cool down to room temperature, open the decompression valve, and absorb the released ammonia gas with dilute hydrochloric acid. The reaction solution was washed three times with 30ml of brine to remove residual ammonia to obtain (S)-2-methylaziridine 94.6g, yield 95%

[0021] (2) Mix and stir 50g of (S)-2-methylaziridine and 1.5g of tetrabutylammonium bisulfate, then cool to 0-3°C at low temperature, add 108g of water dropwise, and control the temperature not to exceed 5°C. The dropwise addition was completed in about 3 hours. Remove t...

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Abstract

The present invention relates to preparation process of (S)-(+)-2-amino propanol. The preparation process includes the following steps: the reaction of (S)-propylene oxide, liquid ammonia and catalyst p-toluene sulfonic acid at 40-120 deg.c and 1-10 MPa to obtain intermediate product (S)-2-methyl aziridine; the subsequent hydrolysis of (S)-2-methyl aziridine under the action of phase transfer catalyst to obtain (S)-(+)-2-amino propanol; and final extracting separation, drying, concentration, and high vacuum distillation and separating purification. The present invention has obviously lowered production cost, no waste produced, no environmental pollution and excellent industrial application foreground.

Description

technical field [0001] The invention relates to a chemical organic synthesis, in particular to a preparation method of (S)-(+)-2-aminopropanol. Background technique [0002] (S)-(+)-2-aminopropanol is an important chiral intermediate in the synthesis of levofloxacin. Levofloxacin is a fully synthetic broad-spectrum antibacterial drug, and its (S) configuration enantiomer has 8-128 times higher antibacterial activity than the (R) configuration enantiomer. It has a 100% curative effect on intestinal infection and gonococcal infection. Because the drug has good curative effect and low toxicity and side effects, it is one of the bulk antibiotic drugs currently used clinically. At present, the main method of producing (S)-(+)-2-aminopropanol at home and abroad is: first esterifying L-alanine, and then reducing it with sodium borohydride and potassium borohydride to obtain the product. However, more than 2 tons of sodium borohydride or potassium borohydride are needed to produc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/08C07C213/02
Inventor 李海林王世运苏宏文
Owner SHANGHAI KELY BIOPHARMACEUTICAL CO LTD