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Method for preparing norephedrine and norpseudoephedrine

A kind of technology of norephedrine and norephedrine, applied in the field of preparing norephedrine and norephedrine

Inactive Publication Date: 2017-03-29
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since this type of compound has two chiral centers, how to obtain optically pure isomers with high stereoselectivity is an urgent problem to be solved.

Method used

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  • Method for preparing norephedrine and norpseudoephedrine
  • Method for preparing norephedrine and norpseudoephedrine

Examples

Experimental program
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Effect test

Embodiment Construction

[0007] Preparation of formula (2) compound

[0008] Add 250mL of phosphate buffered saline solution (0.1mol / L, pH 6.5) and about 60g of chopped fresh carrots into a 500ml Erlenmeyer flask, stir and react at 30°C for about 10min in a water bath constant temperature reactor, and make the plant cells After the oxidoreductase reaches the reaction temperature, 100 mg of the compound of formula (1) is added, and the reaction is continued at 30° C. for 72 hours. The reaction process is monitored by thin-layer chromatography and high-performance liquid chromatography. After the reaction is complete, filter, and the filtrate is extracted three times with 250 mL of ethyl acetate, the organic layers are combined, dehydrated with anhydrous sodium sulfate, concentrated under reduced pressure, and the solvent is removed to obtain the crude product of formula (2), which is separated through a silica gel column to obtain the formula (2) Pure product, yield 85%, 92% ee.

[0009] Compound of f...

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Abstract

The invention relates to a method for preparing (1R, 2S)-norephedrine, (1R, 2R)-norpseudoephedrine and a midbody thereof. The method comprises the following steps: in the reaction process in the first step, by taking a carrot as a medium, carrying out bio-transforming on 2-oximido-1-phenylacetone and reducing into (R)-2-oximido-1-phenyl propyl alcohol; in the second step, reducing (R)-2-oximido-1-phenyl propyl alcohol into a mixture of (1R, 2S)-norephedrine and (1R, 2R)-norpseudoephedrine; adding a chiral reliquid reagent (R)-O-acetyl mandelic acid and decomposing, thereby acquiring an optical pure (1R, 2S)-norephedrine and (1R, 2R)-norpseudoephedrine monomeric compound.

Description

technical field [0001] The present invention relates to the method for preparing norephedrine and norpseudoephedrine Background technique [0002] Norephedrine and norpseudoephedrine are phenethylamine drugs that can stimulate the autonomic nervous system, can be used as cardiovascular drugs, and can also unblock the blocked upper respiratory tract and trachea. However, since this type of compound has two chiral centers, how to obtain optically pure isomers with high stereoselectivity is an urgent problem to be solved. The present invention uses carrot tissue as the medium to carry out the biocatalytic reduction reaction, and obtains synthetic norephedrine and norpseudoephedrine intermediates with a yield of 85% and an ee of 92%. Norephedrine and norpseudoephedrine were obtained with high efficiency. Through crystallization and resolution, we finally successfully obtained norephedrine and norpseudoephedrine, a pair of natural products with good biological activity. Conten...

Claims

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Application Information

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IPC IPC(8): C07C213/02C07C213/10C07C215/30
CPCC07C213/02C07B2200/07C07C213/10C07C249/04C07C215/30C07C251/40
Inventor 孔令义王小兵熊伟偲
Owner CHINA PHARM UNIV
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