A kind of synthetic method of 1-hydroxyl-pyrrolo[2,3-c]piperidine

A synthetic method, 3-c technology, applied in the direction of organic chemistry, etc., can solve the problems of high risk, high production cost, easy to catch fire, etc., and achieve the effect of fewer steps in the reaction process, mild reaction conditions and high yield

Active Publication Date: 2021-05-11
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existing industrialized production route mainly uses dipicolinic acid as its raw material, and a large amount of sodium borohydride is used in the production process, which produces a large amount of borohydroane, which is easy to catch fire, has high production cost and high risk

Method used

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  • A kind of synthetic method of 1-hydroxyl-pyrrolo[2,3-c]piperidine
  • A kind of synthetic method of 1-hydroxyl-pyrrolo[2,3-c]piperidine
  • A kind of synthetic method of 1-hydroxyl-pyrrolo[2,3-c]piperidine

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Embodiment 1

[0041] Step (1): Preparation of 3-(3'-chloropropyl)-4-nitro-1H-pyrrole

[0042] Potassium tert-butoxide (2.24g) was added into a three-necked flask equipped with 20mL THF, and began to cool and stir under an ice bath. When the temperature in the bottle reached -10°C, 1.95g TosMIC (dissolved in 10mLTHF After dropping, continue to stir at -10°C for 1 h. During the reaction, samples are taken for TLC detection. After the reaction is completed, the reaction solution is poured into aqueous ammonium chloride solution for quenching, and diethyl ether (30mL*3) extracts the reaction solution. The ether layers were combined and washed continuously with water. The ether layer was taken, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 1.57 g of compound (VI), with a yield of 84%. NMR ( 1 H NMR, 500MHz, CDCl 3 ) δppm: 1.84 (m, 2H); 2.51 (t, 2H); 3.68 (t, 2H); 6.61 (s, 1H); 7.57 (s, 1H); 9.7 (s, 1H).

[0043] Step (2): Preparation of 3-(N-hydroxyl-amino)-4-(3'-c...

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Abstract

The invention discloses a synthesis method of 1-hydroxy-pyrrolo[2,3-c]piperidine, which adopts the following steps: (1) 1-nitro-5-chloro- 1-pentene is the starting material, reacts with TosMIC shown in formula (Ⅴ) under alkaline conditions to obtain compound (VI); (2) compound (VI) generates compound (VII) through catalytic hydrogenation; (3) Compound (VII) generates compound (III) under the action of a base. The synthesis method of 1-hydroxy-pyrrolo[2,3-c]piperidine of the present invention reduces the process cost and production risk.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to the synthesis of 1-hydroxy-pyrrolo[2,3-c]piperidine. Background technique [0002] Moxifloxacin (trade name: Baifule) whose structure is shown in formula (I) is the fourth generation of quinolone antibacterial drugs, and has a wide antibacterial spectrum: this product is effective against common respiratory pathogens, such as Streptococcus pneumoniae, haemophilus Influenza bacillus, Morahan catarrhalis and some Staphylococcus aureus have strong antibacterial activity. Moreover, the drug has good indication penetration ability and can reach a very high concentration in the lung tissue, so the therapeutic effect is good and the course of treatment is short. In recent years, the domestic sales of moxifloxacin have been gradually increasing every year. [0003] [0004] The key to the synthesis of moxifloxacin bulk drug lies in the synthesis of (S, S)-2,8...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 陈自航宋柳怡方靓琦李景华
Owner ZHEJIANG UNIV OF TECH
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