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Preparation method of high-optical-purity pitavastatin calcium key intermediate

A technology of pitavastatin calcium and intermediates, which is applied in the field of blood lipid-lowering drugs, can solve the problems of low yield, insufficient optical purity of pitavastatin calcium intermediates, and difficult separation and purification, and achieve low cost and high optical purity Effect

Active Publication Date: 2013-11-06
JIANGSU WANBANG BIOPHARMLS +1
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Problems solved by technology

[0006] The present invention aims at the above-mentioned deficiencies existing in the prior art, provides a kind of preparation method of the key intermediate of pitavastatin calcium with high optical purity, solves the problem that the optical purity of the existing pitavastatin calcium intermediate is not high enough, and the E-form stereoselectivity is not high , high difficulty in separation and purification and low yield technical problems

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  • Preparation method of high-optical-purity pitavastatin calcium key intermediate

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Embodiment Construction

[0026] The embodiments of the present invention are described in detail below. This embodiment is implemented on the premise of the technical solution of the present invention, and detailed implementation methods and specific operating procedures are provided, but the protection scope of the present invention is not limited to the following implementation example.

[0027] The preparation of compound IV, reaction formula:

[0028]

[0029] Steps

[0030] In a 25mL Schlenck reaction tube, under a nitrogen atmosphere, add compound II (1.87g, 7.2mmol), compound III (1.00g, 3.6mmol), triphenylphosphine (2.26g, 8.6mmol) and tetrahydrofuran (10mL), and cool to At 0-5°C, diisopropyl azodicarboxylate (1.74g, 8.6mmol) was added dropwise, and after the addition was completed, the mixture was naturally raised to room temperature for 12h. The tetrahydrofuran was distilled off, 20 mL of ethyl acetate and 15 mL of water were added, stirred, left to stand for liquid separation, and the ...

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Abstract

The invention belongs to the technical field of blood fat reducing medicaments and relates to a preparation method of a high-optical-purity pitavastatin calcium key intermediate. The preparation method comprises the following steps of: performing a Mitsunobu reaction on (4R,6S)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-butyl acetate II, a compound III, triphenylphosphine and diisopropyl azodicarboxylate (DIAD) or diethyl azodicarboxylate (DEAD) in a solvent to obtain a compound IV; performing an oxidation reaction to obtain a sulfone compound V; reacting the sulfone compound V with a compound VI under an alkaline environment to obtain the high-optical-purity pitavastatin calcium key intermediate. By the preparation method, the technical problems of low optical purity, low E type stereoselectivity, high separation and purification difficulty and low yield in the conventional pitavastatin calcium intermediate are solved.

Description

technical field [0001] The invention relates to an intermediate in the technical field of blood lipid-lowering drugs and its preparation, in particular to a method for preparing a key intermediate of pitavastatin calcium with high optical purity. Background technique [0002] The disclosed function of pitavastatin calcium is a blood lipid-lowering drug (HMG-CoA reductase inhibitor). The company, in July 2003, was approved to be marketed in Japan for the treatment of hypercholesterolemia, with the trade name "LIVALOR", and the preparation specifications are 1mg and 2mg film-coated tablets. [0003] After searching for the prior art, it was found that Beck et al. reported in Synthesis (synthesis) 1995, pages 1014-1018, that a chiral catalyst was used to carry out asymmetric catalytic hydrogenation of ethyl 4-benzyloxyacetoacetate, and the obtained (S) -Ethyl 4-benzyloxy 3-hydroxybutyrate was subjected to Claisen condensation reaction to obtain (S)-6-benzyloxy-5-hydroxy-butyry...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06
Inventor 张兆国姚莹范为正诸吕锋谢小敏
Owner JIANGSU WANBANG BIOPHARMLS
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