Method for preparing racemic cis-8-benzyl-2, 8-diazabicyclo [4, 3, 0] nonane

A diazabicyclo and racemic technology is applied in the field of preparation of pharmaceutical intermediates, and can solve the problems of affecting the total yield of the reaction, product purity, unsatisfactory catalysis efficiency, and low reactant purity, etc., so as to improve the yield and Product purity, improved selectivity, and improved catalytic activity

Inactive Publication Date: 2020-11-27
SHAYANG QINJIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few researches on (R,R)-8-benzyl-2,8-diazabicyclo[4,3,0]nonane, and the current industry for (R,R)-8- Benzyl-2,8-diazabicyclo[4,3,0]nonane production process recovery yield and the purity of the reactants are generally not high, and in the prior art there is dehydrogenation and re- The method of hydrogenation prepares cis-8-benzyl-2,8-diazabicyclo[4,3,0]nonane racemate, but in the second step hydrogenation reaction, the amount of catalyst is large and the catalytic efficiency Still not ideal, affecting the overall yield of the reaction and the purity of the product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A method for preparing racemic cis-8-benzyl-2,8-diazabicyclo[4,3,0]nonane, comprising the following steps:

[0028] Step S1: Prepare the platinum dehydrogenation catalyst: the noble metal platinum carbon is supported on the solid support silica by impregnation into the impregnation solution containing noble metal ions, and the loading amount of platinum carbon on the solid support is 0.2% of the weight of the solid support. %;

[0029] Step S2: Dehydrogenation of the piperidine ring: (R,R)-8-benzyl-2,8-diazabicyclo[4,3,0]nonane resolved by optical resolution and platinum dehydrogenation catalyst The piperidine ring dehydrogenation reaction was carried out for 3 hours at a weight ratio of 1:0.1 and a reaction temperature of 130° C.;

[0030] Step S3: hydrogenation reaction: the chiral bronsted acid catalyst and the 6-benzyl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]pyridine obtained in step S2 have a ratio of parts by weight of : 0.005:1, in the environment of 40 parts of react...

Embodiment 2

[0032] A method for preparing racemic cis-8-benzyl-2,8-diazabicyclo[4,3,0]nonane, comprising the following steps:

[0033] Step S1: Prepare the platinum dehydrogenation catalyst: the precious metal platinum carbon is supported on the solid carrier porous alumina by impregnation method by impregnating into the impregnating solution containing noble metal ions, and the loading amount of the platinum carbon on the solid carrier is 5% of the weight of the solid carrier %;

[0034] Step S2: Dehydrogenation of the piperidine ring: (R,R)-8-benzyl-2,8-diazabicyclo[4,3,0]nonane resolved by optical resolution and platinum dehydrogenation catalyst The piperidine ring dehydrogenation reaction was carried out for 5 hours at a ratio of 1:2 by weight and a reaction temperature of 140° C.;

[0035] Step S3: hydrogenation reaction: the chiral bronsted acid catalyst and the 6-benzyl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]pyridine obtained in step S2 have a ratio of parts by weight of : 0.01:1, in t...

Embodiment 3

[0037] A method for preparing racemic cis-8-benzyl-2,8-diazabicyclo[4,3,0]nonane, comprising the following steps:

[0038] Step S1: Prepare the platinum dehydrogenation catalyst: the noble metal platinum carbon is supported on the solid support silica-alumina gel by impregnation method by immersion into the impregnation solution containing noble metal ions, and the loading amount of platinum carbon on the solid support is 2% of the weight of the solid support. %;

[0039] Step S2: Dehydrogenation of the piperidine ring: (R,R)-8-benzyl-2,8-diazabicyclo[4,3,0]nonane resolved by optical resolution and platinum dehydrogenation catalyst The piperidine ring dehydrogenation reaction was carried out for 4 hours at a ratio of 1:1 by weight and a reaction temperature of 135° C.;

[0040] Step S3: hydrogenation reaction: the chiral bronsted acid catalyst and the 6-benzyl-1,2,3,4-tetrahydro-pyrrolo[3,4-b]pyridine obtained in step S2 have a ratio of parts by weight of : 0.008:1, in the e...

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PUM

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Abstract

The invention provides a method for preparing racemic cis-8-benzyl-2, 8-diazabicyclo [4, 3, 0] nonane. The method comprises the following steps of: step S1, preparing a platinum dehydrogenation catalyst; S2, catalyzing piperidine cyclic dehydrogenation reaction by adopting the platinum dehydrogenation catalyst; and S3, carrying out a catalytic hydrogenation reaction by using a chiral brominated acid catalyst. The method for preparing the racemic cis-8-benzyl-2, 8-diazabicyclo [4, 3, 0] nonane of the invention is high in raceme purity and high in reaction yield.

Description

technical field [0001] The invention relates to the field of preparation of pharmaceutical intermediates, in particular to a method for preparing 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-diaza...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07B2200/07C07D471/04
Inventor 朱广友田艳英
Owner SHAYANG QINJIANG CHEM
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