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Preparation of racemic cis 8-benzyl-2,8-diazabicyclo[4,3,0]nonane

A diazabicyclic and racemic technology, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of low reaction selectivity, low catalytic efficiency, and affecting product purity, so as to improve catalytic efficiency, selectivity and Sufficiency of reaction, effect of improving purity

Active Publication Date: 2022-01-14
SHAYANG QINJIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the first step, manganese dioxide has the problems of low catalytic efficiency and low reaction selectivity as a catalyst, which affects the purity of the product.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation process of racemic cis 8-benzyl-2,8-diazabicyclo[4,3,0]nonane comprises the following steps:

[0029] Step S1: preparing an attachment carrier: immersing the solid carrier into a roughening solution to prepare an attachment carrier, the roughening solution being sodium hydroxide solution or sodium bifluoride solution;

[0030] Step S2: preparing a platinum dehydrogenation catalyst: using an impregnation method to load noble metal platinum on a silica solid support by impregnating into an impregnating solution containing noble metal ions, in parts by weight, the impregnating solution includes chloroplatinic acid 30 1 part, 1 part of rice furoic acid, 1 part of dichlorophenyl imidazole dioxolane, the load on the solid carrier is 0.1% of the weight of the solid carrier;

[0031] Step S3: Dehydrogenation reaction of piperidine ring: (R,R)-8-benzyl-2,8-diazabicyclo[4,3,0]nonane obtained by optical resolution and platinum dehydrogenation catalyst At a reactio...

Embodiment 2

[0034] The preparation process of racemic cis 8-benzyl-2,8-diazabicyclo[4,3,0]nonane comprises the following steps:

[0035] Step S1: preparing an attachment carrier: immersing the solid carrier into a roughening solution to prepare an attachment carrier, the roughening solution being sodium hydroxide solution or sodium bifluoride solution;

[0036] Step S2: preparing a platinum dehydrogenation catalyst: the noble metal platinum is supported on the porous alumina solid support by impregnation into an impregnation solution containing noble metal ions by impregnation method, and the impregnation solution includes chloroplatinic acid 40 5 parts, 5 parts of rice furoic acid, 3 parts of dichlorophenyl imidazole dioxolane, the load on the solid carrier is 5% of the weight of the solid carrier;

[0037] Step S3: Dehydrogenation reaction of piperidine ring: (R,R)-8-benzyl-2,8-diazabicyclo[4,3,0]nonane obtained by optical resolution and platinum dehydrogenation catalyst At a reaction ...

Embodiment 3

[0040] The preparation process of racemic cis 8-benzyl-2,8-diazabicyclo[4,3,0]nonane comprises the following steps:

[0041] Step S1: preparing an attachment carrier: immersing the solid carrier into a roughening solution to prepare an attachment carrier, the roughening solution being sodium hydroxide solution or sodium bifluoride solution;

[0042] Step S2: Prepare the platinum dehydrogenation catalyst: use the impregnation method to load the noble metal platinum on the silica-alumina colloidal solid support by impregnating into the impregnating solution containing noble metal ions. The impregnating solution includes chloroplatinic acid 35 3 parts, 3 parts of rice furoic acid, 2 parts of dichlorophenyl imidazole dioxolane, the load on the solid carrier is 2% of the weight of the solid carrier;

[0043] Step S3: Dehydrogenation reaction of piperidine ring: (R,R)-8-benzyl-2,8-diazabicyclo[4,3,0]nonane obtained by optical resolution and platinum dehydrogenation catalyst At a re...

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Abstract

The invention provides a preparation process for racemic cis-8-benzyl-2,8-diazabicyclo[4,3,0]nonane, which comprises the following steps: Step S1: preparing an attachment carrier: immersing a solid carrier into Prepare an attachment carrier in a roughening solution, the roughening solution is a sodium hydroxide solution or a sodium bifluoride solution; Step S2: Prepare a platinum dehydrogenation catalyst: use an impregnation method to support the precious metal platinum by impregnating it into an impregnation solution containing noble metal ions On the solid carrier, in parts by weight, the impregnation solution includes 30-40 parts of chloroplatinic acid and 1-5 parts of rice furoic acid; step S3: piperidine ring dehydrogenation reaction; step S4: high-pressure hydrogenation reaction. The invention provides a method for preparing racemic cis-8-benzyl-2,8-diazabicyclo[4,3,0]nonane with high selectivity, high catalytic efficiency and high product purity.

Description

technical field [0001] The invention relates to the field of preparation of pharmaceutical intermediates, in particular to a preparation process of racemic cis 8-benzyl-2,8-diazabicyclo[4,3,0]nonane. Background technique [0002] Moxifloxacin is a new type of fluoroquinolones. Its chemical structure is significantly different from other fluoroquinolones. The 8-position carbon atom of the quinolone core is introduced into a methoxy group, and the 7-position carbon atom is introduced into -benzyl-2,8 -Diazabicyclo[4,3,0]nonane, which enhances the drug's activity against Gram-positive aerobic bacteria without causing significant phototoxicity, increases its solubility, and reduces the risk of crystalluria formation . The existence of these substituents makes the drug have a broad-spectrum antibacterial effect, which has been used as a chemotherapeutic agent for humans and animals, and can effectively treat infections caused by various bacteria. [0003] (S,S)-8-benzyl-2,8-dia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04B01J23/42B01J31/02B01J31/04B01J33/00B01J37/02
CPCC07D471/04B01J31/0244B01J31/04B01J37/0207B01J37/0203B01J31/0271B01J33/00B01J23/42
Inventor 朱广友田艳英
Owner SHAYANG QINJIANG CHEM
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