Method for measuring optical purity of (R)-3-quinuclidinol

A technology of optical purity and determination method, applied in the field of medicine and chemical industry, can solve the problems of difficult chiral chromatographic separation, lack of groups, inapplicability, etc., and achieve the effect of good peak purity and enhanced identification ability.

Active Publication Date: 2014-11-05
JINAN ASIA PHARMA TECH
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Problems solved by technology

Tracing it to its cause, because (R)-3-quinuclidinol has no ultraviolet absorption on the one hand, is not suitable for routine liquid chromato

Method used

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  • Method for measuring optical purity of (R)-3-quinuclidinol
  • Method for measuring optical purity of (R)-3-quinuclidinol
  • Method for measuring optical purity of (R)-3-quinuclidinol

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Embodiment 1

[0049] The method for measuring the optical purity of R-3-quinuclidinol is as follows:

[0050] (A) Sample preparation:

[0051] (A1) Preparation of (RS)-3-quinuclidinyl p-toluenesulfonate:

[0052] Add 30 mL of DCM, 5 g of 3-quinuclidinol and 11.5 g of TEA to a 100 mL reaction flask, cool to 0°C, and slowly add a solution of 11 g of p-toluenesulfonyl chloride and 30 mL of DCM at 0-5°C while stirring, and finish dropping. Slowly rise to room temperature, continue to stir the reaction until TLC detects the reaction is complete, cool to 0°C, slowly add 30 mL of water with stirring, separate the layers, wash the organic layer once with 50 mL of water, wash once with 50 mL of saturated sodium chloride solution, and dry. After filtration, the filtrate was concentrated until no liquid dripped out, and purified by column chromatography to obtain a slightly yellow solid, namely (RS)-3-quinuclidinyl p-toluenesulfonate, 8 g in total, with a yield of 68%;

[0053] (A2) Preparation of (R)-3-quin...

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Abstract

The invention belongs to the technical field of pharmaceutical chemical engineering, and in particular relates to a method for measuring the optical purity of (R)-3-quinuclidinol. The method for measuring the optical purity of (R)-3-quinuclidinol comprises the steps of (a) preparing a sample; (b) preparing a test solution; (c) preparing a chromatographic condition, and performing detection. According to the method, a precolumn derivatization chiral chromatography method is adopted to measure the optical purity of (R)-3-quinuclidinol; specifically, the precolumn derivatization method is used for enabling (RS)-3-quinuclidinol racemate and paratoluensulfonyl chloride to react to generate (RS)-3-quinuclidinol paratoluensulfonyl chloride derivative, namely quinuclidinol 3-paratoluene sulfonate; then the chiral chromatography method is used for measuring the optical purity; therefore, the technical difficulty in measurement of the optical purity of (R)-3-quinuclidinol is creatively solved.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a method for measuring the optical purity of R-3-quinuclidinol. Background technique [0002] The chemical name of (R)-3-quinuclidinol is 1-azacyclo[2.2.2]octane(R)-3-ol, which is a synthetic muscarinic receptor antagonist such as solifenacin, Important intermediates of valtropate, tasalidine, etc., the structural formula of R-3-quinuclidin is as follows: . [0003] The synthesis of (R)-3-quinuclidinol is to use 3-quinuclidinone as raw material to generate (RS)-3-quinuclidinol through carbonyl reduction, and then obtain (R)-3-quinuclidinol through resolution Niclidinol, the purity of (R)-3-quinuclidinol after resolution is described by measuring the optical rotation and calculating the ee value. The method of measuring the optical rotation to calculate ee has a large error in the determination of the optical purity of (R)-3-quinuclidinol. Fi...

Claims

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Application Information

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IPC IPC(8): G01N30/02
Inventor 彭立增李冬梅孙建林
Owner JINAN ASIA PHARMA TECH
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