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Method for chiral synthesis of (S,S)-2-8-diazabicyclononane

A technology of chiral synthesis and chiral separation, applied in the direction of organic chemistry, etc., can solve the problems of long reaction route, low production efficiency, late separation steps, etc., to save raw materials and reagents, improve efficiency, and reduce costs.

Active Publication Date: 2013-03-06
CHONGQING HUABANGSHENGKAI PHARM
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Problems solved by technology

[0012] As can be seen from the prior art method, not only the steps are many, the reaction route is long, but also the resolution step is late, resulting in low final product yield, low production efficiency, and high production cost

Method used

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  • Method for chiral synthesis of (S,S)-2-8-diazabicyclononane
  • Method for chiral synthesis of (S,S)-2-8-diazabicyclononane
  • Method for chiral synthesis of (S,S)-2-8-diazabicyclononane

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Embodiment 1

[0048] Embodiment 1 (S, S)-2, the preparation of 8-diazabicyclo [4.3.0] nonane (formula I)

[0049] 1.1 Hydrogenation reaction

[0050] Dissolve 100g of methyl 2,3-pyridinedicarboxylate in 500mL of toluene, then transfer it into an autoclave, add 5g of 10% palladium carbon, the system is closed, and after three times of hydrogen replacement, keep the stirring speed at 500 rpm and the system pressure React at 1 MPa and 50-60°C for 5 hours, lower the temperature to release excess hydrogen, filter the reaction solution, and distill the filtrate to remove toluene to obtain 101 g of almost colorless liquid with a yield of 98%.

[0051] The product was identified as cis-2,3-piperidine-dicarboxylic acid methyl ester by NMR, and the NMR data was:

[0052] 1 H NMR (500MHz, CDCl 3 ): δ1.48-1.53(m, 2H), 1.77-1.82(m, 1H), 2.14-2.18(m, 1H), 2.26(br, 1H), 2.67-2.72(m, 1H), 2.99-3.07( m, 2H), 3.65 (d, J = 3.5 Hz, 1H), 3.70 (s, 3H), 3.75 (s, 3H).

[0053] 1.2 Split reaction

[0054] Tak...

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Abstract

The invention provides a method for chiral synthesis of (S,S)-2-8-diazabicyclo[4.3.0]nonane. A target product with a desired structure is prepared by using pyridine 2,3-diformate as a raw material and carrying out a four-step reaction comprising hydrogenation, resolution, aminolysis and reduction. According to the method, a synthetic route is simple and short, the step of resolution is carried out at an early stage, and reaction raw materials and reagents are saved; thus, production cost is reduced, and production efficiency is improved.

Description

technical field [0001] The invention relates to a synthesis method of a chiral compound, in particular to a synthesis method of the chiral compound (S, S)-2,8-diazabicyclo[4.3.0]nonane. Background technique [0002] 2,8-diazabicyclo[4.3.0]nonane is a saturated heterocyclic compound and also a chiral compound, which exists in (2S, 8S), (2R, 8S), (2S, 8R), ( 2R, 8R) and other chiral isomers. [0003] One of the configurations (S, S)-2,8-diazabicyclo[4.3.0]nonane (formula I) is an important side chain of the antibacterial drug moxifloxacin (moxifloxacin chemical name: 1- Cyclopropyl-7-(S,S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4- dihydro-3-quinolinecarboxylic acid). Therefore, the synthesis of formula I has become the focus of moxifloxacin synthesis research. [0004] [0005] The formula I is a chiral compound, and the step of chiral resolution of various isomer products must be encountered in the synthesis. In the prior art, the compound of for...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 张波
Owner CHONGQING HUABANGSHENGKAI PHARM
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