Preparation method of moxifloxacin intermediate

A technology for moxifloxacin and intermediates is applied in the field of preparation of moxifloxacin intermediates, which can solve the problems of highly toxic hydrogen fluoride smog, high equipment requirements, short reaction time, etc. Environmentally friendly effects

Inactive Publication Date: 2014-02-19
SICHUAN UNIV
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Problems solved by technology

6-Benzyl-hexahydro-pyrrolo[3,4-b]pyridine-5,7-dione (II) and 6-benzyl-octahydro-pyrrolo[3,4-b]pyridine (I) They are all key intermediates for synthesizing moxifloxacin. There are many reports on their synthetic methods, but they lack high safety and are suitable for industrial production.
[0006] CN101591336A reported the metal borohydride/BF3 reduction system for 6-benzyl-hexahydro-pyrrolo[3,4 -b] Reduction of pyridine-5,7-dione and its chiral isomers, the yield is 72%-91%, but the reduction system of BF3 is exposed to water or placed in humid air Decompose immediately t

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  • Preparation method of moxifloxacin intermediate

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Embodiment 1

[0027] Example 1: Synthesis of 6-benzyl-octahydro-pyrrolo[3,4-b]pyridine

[0028] Add 6-benzyl-hexahydro-pyrrolo[3,4-b]pyridine-5,7-dione (50g, 0.2mol) and 400ml tetrahydrofuran into a 3L three-necked flask and cool to 0-5°C , adding NaBH in batches 4 (37g, 1.0mol). After the addition is complete, slowly add 400 ml of concentrated sulfuric acid (49 g, 0.5 mol) in tetrahydrofuran dropwise at 0°C, controlling the internal temperature to not exceed 10°C. After dropping, the temperature was slowly raised to room temperature for 12 hours. Add 500ml of tetrahydrofuran and 500ml of water to dilute the reaction solution, add 49% sulfuric acid solution dropwise at 0°C, adjust the pH to 2, and reflux for 1h. Cool to 0°C, add solid sodium hydroxide to adjust the pH to 10, stir at room temperature for 30 min, extract with ethyl acetate three times, wash with saturated brine once, dry and concentrate to obtain 39 g of light yellow oily liquid with a yield of 88.3%. 1 H NMR (400MHz, CDC...

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Abstract

The invention discloses a preparation method of a moxifloxacin intermediate 6-benzyl-octahydro-pyrrolo[3,4-b]pyridine (as shown in formula I). The preparation method is to adopt an NaBH4/H2SO4 reducing system to reduce 6-benzyl-hexahydro-pyrrolo[3,4-b]pyridine-5,7-dione (as shown in formula II), so as to obtain the target product. The method can be processed at normal temperature and normal pressure to take reaction with high total recovery; the raw material is cheap, easy to get, and easy to store; the operation is simple; the safety is high.

Description

technical field [0001] The invention relates to a method for preparing a moxifloxacin intermediate 6-benzyl-octahydro-pyrrolo[3,4-b]pyridine. Background technique [0002] The structure type of Moxifloxacin belongs to quinolones. Its chemical name is: 1-cyclopropyl-7-﹛(S,S)-2,8-diazo-bicyclo[4.3.0]non-8-yl﹜-6-fluoro-8-methoxy -1,4-Dihydro-4-oxo-3-quinolinecarboxylic acid. [0003] [0004] Moxifloxacin is the fourth-generation quinolone antibacterial drug. The biggest difference from other quinolone drugs is that a methoxy group is introduced into its 8-position carbon atom. It is based on this structural feature that it not only It has the activity of quinolones against Gram-negative bacteria, and also enhances the antibacterial effect against Gram-positive bacteria and atypical pathogenic bacteria, and has no obvious phototoxicity. Due to its high solubility, it reduces the risk of crystalluria formation . 6-Benzyl-hexahydro-pyrrolo[3,4-b]pyridine-5,7-dione (II) and...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 郭丽吴勇海俐邱瑞李晓岑
Owner SICHUAN UNIV
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