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Preparation method of (S,S)-2, 8-diazabicyclo[4,3,0] nonane

A diazabicyclo and nonane technology, applied in the -2 field, can solve the problems of high cost, high yield, and many steps, achieve good yield, shorten the process flow, and improve economic benefits

Inactive Publication Date: 2012-07-25
浙江凯迪药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This route has more steps, higher cost and higher yield

Method used

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  • Preparation method of (S,S)-2, 8-diazabicyclo[4,3,0] nonane
  • Preparation method of (S,S)-2, 8-diazabicyclo[4,3,0] nonane
  • Preparation method of (S,S)-2, 8-diazabicyclo[4,3,0] nonane

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Embodiment 1

[0040] A preparation method of (S, S)-2,8-diazabicyclo[4,3,0]nonane, comprising:

[0041] (1) Preparation of 2,3-dichloromethylpyridine hydrochloride

[0042] Under nitrogen protection, 2,3-lutidine (9.4g, 0.088mol) and N-chlorosuccinimide (24g, 0.180mol) were dissolved in CCl with stirring 4 (900ml), 200w UV lamp irradiation for 24h, cooling (0-5 ℃) the reaction solution, remove succinimide and unreacted N-chlorosuccinimide, then add an equivalent amount of N-chlorobutane Diimide (24g, 0.180mol), react for another 24h; cool (0-5°C) the reaction solution and filter, then pass through excess anhydrous HCl, filter, and the filter cake after filtration is recrystallized in isopropanol to obtain The crude hydrochloride of 2,3-dichloromethylpyridine (14.3g, 0.0724mol), the yield is 82%;

[0043] (2) Preparation of 6-benzyl-pyrrolo[3,4-b]pyridine

[0044] At room temperature, 2,3-dichloromethylpyridine hydrochloride (17g, 0.097mol) prepared in step (1) was dissolved in acetonitri...

Embodiment 2

[0050] A preparation method of (S, S)-2,8-diazabicyclo[4,3,0]nonane, comprising:

[0051] (1) Preparation of 2,3-dichloromethylpyridine hydrochloride

[0052] Under nitrogen protection, 2,3-lutidine (9.4 g, 0.088 mol) and N-chlorosuccinimide (0.225 mol) were dissolved in CCl with stirring 4 (1000ml), 200w UV lamp irradiation for 28h, cooling (0-5 ℃) reaction solution, remove succinimide and unreacted N-chlorosuccinimide, then add an equivalent amount of N-chlorobutane Diimide (0.225mol), and then reacted for 28h; cooled (0-5°C) the reaction solution and filtered, then passed through an excess of anhydrous HCl, filtered, and the filtered filter cake was recrystallized in isopropanol to obtain 2, The hydrochloride crude product of 3-dichloromethylpyridine (14.1g, 0.0716mol), the yield is 81%;

[0053] (2) Preparation of 6-benzyl-pyrrolo[3,4-b]pyridine

[0054] At room temperature, 2,3-dichloromethylpyridine hydrochloride (17g, 0.097mol) prepared in step (1) was dissolved in a...

Embodiment 3

[0060] Steps (2), (3), (4) are the same as (2), (3), (4) steps of Example 1, and different from Example 1 step (1), 2,3-dimethyl The molar ratio of pyridine to N-chlorosuccinimide added for the first time is 0.6; the final product is (S, S)-2,8-diazabicyclo[4,3,0]nonane in the form of yellow mucus, Overall yield was 23%, ee>99%.

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Abstract

The invention relates to a preparation method of (S,S)-2, 8-diazabicyclo[4,3,0] nonane. The preparation method comprises the following steps: taking 2,3-dimethylpyridine as a raw material, performing halogenation on 2,3-dimethylphyridine through N-chloro succinimide to be in cyclization with benzylamine, performing hydrogenation on pyridine ring and removing benzyl groups, and finally performing chiral resolution to obtain the (S,S)-2, 8-diazabicyclo[4,3,0] nonane. According to the invention, the preparation method has advantages of short process flow, low cost and high yield, reaches total yield of 23% and ee value of above 99% and is safe and reliable, thereby being applicable in industrial production.

Description

technical field [0001] The invention relates to the field of preparation of moxifloxacin intermediates, in particular to a preparation method of (S, S)-2,8-diazabicyclo[4,3,0]nonane. Background technique [0002] Moxifloxacin (moxifloxacin), the chemical name is 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS, 7aS)-octahydro-6H-pyrrolo[ 3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid is a fourth-generation fluoroquinolone antibacterial drug developed by Bayer Company in Germany, and its hydrochloride is used clinically. This product was first launched in Germany in September 1999, and in the United States in December of the same year, for the treatment of acute sinus adenitis, acute exacerbation of chronic bronchitis, community-acquired pneumonia, and uncomplicated skin infections and skin and soft tissue infections . Its chemical formula is (I). (S, S)-2,8-diazabicyclo[4,3,0]nonane is the side chain of moxifloxacin and is the key intermediate for the synthesis ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 高金华吴庆安
Owner 浙江凯迪药业有限公司
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