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Method for resolving R/S-3-quinuclidinol by adopting precolumn derivation high performance liquid chromatography

A high-performance liquid chromatography, S-3-technology, applied in the field of resolution of R/S-3-quinuclidinol, to achieve the effect of improving peak shape, fast and sensitive detection, and good resolution

Active Publication Date: 2015-04-08
上海柏狮生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the present invention is to provide a kind of technical problem in order to solve above-mentioned complicated operation, long cycle, high cost, low sensitivity, chromatographic peak separation degree and symmetry etc. The method of separating R / S-3-quinuclidinol by pre-column derivatization high-performance liquid chromatography can overcome the defects and deficiencies of existing analytical methods, making the operation simple and convenient, rapid and sensitive detection, and chromatographic peak shape With good symmetry and high resolution, R / S-3-quinuclidinol can be detected and resolved more effectively

Method used

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  • Method for resolving R/S-3-quinuclidinol by adopting precolumn derivation high performance liquid chromatography
  • Method for resolving R/S-3-quinuclidinol by adopting precolumn derivation high performance liquid chromatography
  • Method for resolving R/S-3-quinuclidinol by adopting precolumn derivation high performance liquid chromatography

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Embodiment 1

[0030] A method utilizing pre-column derivation high performance liquid chromatography to resolve R / S-3-quinuclidinol, specifically comprising the steps of:

[0031] (1) R / S-3-quinuclidinol is derivatized and esterified before the column to obtain R / S-3-quinuclidinol ester, and the obtained R / S-3-quinuclidinol ester, its The structural formula is as follows:

[0032]

[0033] where R is COC 6 h 5 ;

[0034] The pre-column derivatization esterification is about R / S-3-quinuclidinol and aromatic acid in ethyl acetate solvent, DMF is used as a catalyst for esterification to obtain R / S-3-quinuclidinol ester;

[0035] The amount of aromatic acid, R / S-3-quinuclidinol and catalyst used in the above-mentioned esterification is calculated in molar ratio, that is, aromatic acid: R / S-3-quinuclidinol: DMF is 1:1:0.1 ;

[0036] Wherein said aromatic acid is benzoic acid;

[0037] The above-mentioned pre-column derivative esterification reaction specifically comprises the steps:

...

Embodiment 2

[0051] A method utilizing pre-column derivation high performance liquid chromatography to resolve R / S-3-quinuclidinol, specifically comprising the steps of:

[0052] (1) R / S-3-quinuclidinol is derivatized and esterified before the column to obtain R / S-3-quinuclidinol ester, and the obtained R / S-3-quinuclidinol ester, its The structural formula is as follows:

[0053]

[0054] where R is COC 10 h 7 ;

[0055] The pre-column derivatization esterification is about R / S-3-quinuclidinol and aromatic acid in ethyl acetate solvent, DMF is used as a catalyst for esterification to obtain R / S-3-quinuclidinol ester;

[0056] The amount of aromatic acid, R / S-3-quinuclidinol and catalyst used in the above-mentioned esterification is calculated in molar ratio, that is, aromatic acid: R / S-3-quinuclidinol: DMF is 1:1:0.1 ;

[0057] Wherein said aromatic acid is 1-naphthoic acid;

[0058] The above-mentioned pre-column derivative esterification reaction specifically comprises the steps...

Embodiment 3

[0076] A method utilizing pre-column derivation high performance liquid chromatography to resolve R / S-3-quinuclidinol, specifically comprising the steps of:

[0077](1) R / S-3-quinuclidinol is derivatized and esterified before the column to obtain R / S-3-quinuclidinol ester, and the obtained R / S-3-quinuclidinol ester, its The structural formula is as follows:

[0078]

[0079] where R is COC 6 h 4 OCH 3 ;

[0080] The pre-column derivatization esterification is about R / S-3-quinuclidinol and aromatic acid in ethyl acetate solvent, DMF is used as a catalyst for esterification to obtain R / S-3-quinuclidinol ester;

[0081] The amount of aromatic acid, R / S-3-quinuclidinol and catalyst used in the above-mentioned esterification is calculated in molar ratio, that is, aromatic acid: R / S-3-quinuclidinol: DMF is 1:1:0.1 ;

[0082] Wherein said aromatic acid is p-methoxybenzoic acid;

[0083] The above-mentioned pre-column derivative esterification reaction specifically comprises...

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Abstract

The invention discloses a method for resolving R / S-3-quinuclidinol by adopting a precolumn derivation high performance liquid chromatography. The method comprises the following steps of firstly, carrying out precolumn derivation esterification reaction on R / S-3-quinuclidinol to obtain R / S-3-quinuclidinol ester; then, preparing a 1.0mg / mL sample solution from R / S-3-quinuclidinol ester by using a high performance liquid chromatograph, wherein an amylose chiral column is used as a chromatographic column, a mixed solution of n-hexane, an alcohol and an alkaline additive is used as a positive mobile phase, and the flow rate, the sample volume, the detection wavelength and the chromatographic column temperature are controlled at 0.6-1mL / min, 5mul, 220-280nm and 20-35 DEG C respectively; and resolving the R / S-3-quinuclidinol ester chirally. The chromatographic peak obtained by adopting the method is good in pattern and symmetry and high in degree of resolving, and the method can be used for detecting and resolving R / S-3-quinuclidinol efficiently, rapidly and sensitively.

Description

technical field [0001] The invention relates to a method for separating R / S-3-quinuclidinol by pre-column derivatization high-performance liquid chromatography, that is, derivatizing R / S-3-quinuclidinol before the column to obtain derivatives with ultraviolet absorption , and then the derivatives were separated and detected by chiral chromatographic column and ultraviolet detector. Background technique [0002] The chemical name of R-3-quinuclidin is 1-azacyclo-[2,2,2]-octyl-R-3-ol, which is used to study human erythrocyte acetylcholinesterase and synthesize several muscarinic receptors It is an important intermediate of body antagonist drugs such as solifenacin, ravatorate, tasalidine, etc. It is also the precursor of chiral liquid catalysts and is widely used in chiral catalysis. At present, most drugs are mainly administered as racemates, and the administration of optically pure enantiomers is the development trend of most chiral drugs. Therefore, the research on the c...

Claims

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Application Information

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IPC IPC(8): G01N30/02
Inventor 潘仙华张瑞敏于一文徐斯尧陈思羽刘烽徐娜
Owner 上海柏狮生物科技有限公司
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