Novel preparation method of azabicyclo medical intermediate

A technology of azabicyclo and intermediates, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of high production costs, achieve the effects of reduced dosage, reduced industrial waste water, and high yields

Active Publication Date: 2022-02-11
ZHEJIANG NHU CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] This method requires the use of a large amount of expensive lithium aluminum hydride reducing agent to reduce caronic anhydride to obtain 6,6-dimethyl-3-azabicyclo[3.1.0]hexane, and the production cost is high

Method used

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  • Novel preparation method of azabicyclo medical intermediate
  • Novel preparation method of azabicyclo medical intermediate
  • Novel preparation method of azabicyclo medical intermediate

Examples

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preparation example Construction

[0113] Furthermore, the synthetic method of the present invention further includes:

[0114] i) amination reaction of the compound of the general formula (2-1) to obtain the compound of the general formula (3); and

[0115] ii) subjecting the compound of general formula (3) to a reduction reaction to obtain a compound of general formula (4),

[0116]

[0117] Wherein, the definition of R is the same as that defined in the general formula (1).

[0118] In step i, the specific conditions of the amination reaction are not particularly limited, and conventional amination reaction conditions in the art can be used.

[0119] In some specific embodiments of the present invention, the amination reaction is carried out with the aid of an alcoholic solvent of ammonia gas, and the alcoholic solvent is preferably methanol from the viewpoint of convenience.

[0120] Typically, the compound of general formula (2-1) can be dissolved in an alcoholic solvent, and an ammonia-alcohol reagen...

Embodiment 1

[0148] Embodiment 1 (preparation of intermediate formula a)

[0149] Add 196mg of cuprous chloride to a 200mL flask, add 680mg of ligand L1, add 100mL of dichloroethane solution, stir at room temperature for 1h, raise the temperature to 75°C, and slowly add 15.4g of

[0150]

[0151] Compound 3h, the product intermediate formula a was evaporated under reduced pressure after the reaction, the yield was 93.1%, and the ratio of cis-form and trans-form was greater than 100:1.

Embodiment 2～14

[0152] Examples 2-14 (preparation of intermediate formula a)

[0153] The difference from Example 1 is that the control of the reaction parameters is different, and the specific reaction parameters and reaction effects are shown in Table 1.

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Abstract

The invention relates to an azabicyclo medical intermediate, in particular to a synthesis method of 6,6-dimethyl-3-azabicyclo[3.1.0] hexane or a derivative thereof. A hetero-atom bicyclic compound is constructed through cyclization of an intra-molecular diazo group and an olefin bond, and a target product is finally obtained through an amination reaction and a reduction reaction.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, in particular to a preparation method of a medicine intermediate, in particular to a medicine intermediate 6,6-dimethyl-3-azabicyclo[3.1.0]hexane or its derivatives Preparation Background technique [0002] Pharmaceutical intermediate compounds are an important link in the supply chain in the pharmaceutical industry. The stability of the supply chain's output and quality has been paid more and more attention by the entire industry, especially during the period when the epidemic of infectious diseases has led to a sharp increase in the demand for pharmaceuticals. [0003] It is known that 6,6-Dimethyl-3-azabicyclo[3.1.0]hexane (6,6-Dimethyl-3-azabicyclo[3.1.0]hexane; CAS No.: 943516-54-9 ) is an important pharmaceutical intermediate, which is an important raw material used in the synthesis of many drugs such as the hepatitis C protease inhibitor Boceprevir (Boceprevir) and the oral d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/52A61P31/14
CPCC07D209/52A61P31/14
Inventor 张玉红于洋石清爱黄国东李浩然朱根林刘晓庆胡瑞君
Owner ZHEJIANG NHU CO LTD
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