A method for separating r/s-3-quinuclidinol by pre-column derivatization 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 improved peak shape, fast and sensitive detection, chromatographic peak shape and good symmetry

Active Publication Date: 2016-03-23
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 utilizing pre-column derivatization high-performance liquid chromatography to resolve R / S- The method of 3-quinuclidinol, which can overcome the defects and deficiencies of the existing analytical methods, makes the operation simple and convenient, rapid and sensitive detection, good chromatographic peak shape and symmetry, high resolution, and more effective detection and split R / S-3-quinuclidinol

Method used

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  • A method for separating r/s-3-quinuclidinol by pre-column derivatization high performance liquid chromatography
  • A method for separating r/s-3-quinuclidinol by pre-column derivatization high performance liquid chromatography
  • A method for separating r/s-3-quinuclidinol by pre-column derivatization high performance liquid chromatography

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Experimental program
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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 following steps:

[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 ste...

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 OCH3 ;

[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 pre-column derivatization high-performance liquid chromatography, that is, firstly, R / S-3-quinuclidinol is obtained through pre-column derivatization esterification reaction R / S-3-quinuclidinol ester, then use high-performance liquid chromatography, using amylose chiral column as chromatographic column, using a mixture of n-hexane, alcohol and alkaline additives as the normal phase mobile phase , the above-mentioned R / S-3-quinuclidinol ester was made into a sample solution with a concentration of 1.0 mg / mL, the flow rate was controlled to be 0.6-1 mL / min, the injection volume was 5 μL, and the detection wavelength was 220-280 nm. The column temperature is 20-35°C, and the above-obtained R / S-3-quinuclidinyl ester is subjected to chiral separation. The chromatographic peak shape and symmetry obtained by the separation method are better, and the separation degree is higher, and the R / S-3-quinuclidinol ester can be effectively, rapidly and sensitively detected and resolved.

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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Patent Type & Authority Patents(China)
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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