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Scalable synthesis of optically active 1-cyclopropylalkyl-1-amines

A technology of cyclopropyl alkyl and alkyl, applied in the direction of reductive alkylation preparation, organic chemistry, chemical instruments and methods, etc.

Pending Publication Date: 2021-06-08
BOEHRINGER INGELHEIM INT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of low-temperature Grignard reactions and purification by flash chromatography are disadvantages in view of larger scale production

Method used

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  • Scalable synthesis of optically active 1-cyclopropylalkyl-1-amines
  • Scalable synthesis of optically active 1-cyclopropylalkyl-1-amines
  • Scalable synthesis of optically active 1-cyclopropylalkyl-1-amines

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Embodiment Construction

[0010] In a first aspect, the present invention provides a method for the preparation of non-racemic 1-cyclopropylalkyl-1-amines of formula I, such as (S)-1-cyclopropylalkyl-1-amine method

[0011]

[0012] It includes compounds of formula II

[0013]

[0014] Reaction with a compound of formula III

[0015]

[0016] where R 1 and R 2 independently is C 1 -C 6 -alkyl.

[0017] In another aspect, the process for preparing 1-cyclopropylalkyl-1-amines of formula I comprises the step of: i) condensing a compound of formula II with a compound of formula III to form an imine of formula INT1 , ii) reduction to the corresponding secondary amine of formula INT2, and iii) debenzylation to the primary amine of formula I as described.

[0018]

[0019] Preferred reaction conditions for step i) include the use of a Lewis acid in a suitable solvent.

[0020] Examples of solvents that can be used in reaction step i) include methanol, ethanol, isopropanol, benzene, toluene...

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Abstract

The present invention provides a new, scalable synthetic method for the preparation of non-racemic 1-cyclopropyl alkyl-1-amines, e.g. (S)-1-cyclopropyl ethyl-1-amine. The method makes use of inexpensive starting materials (such as cyclopropyl methyl ketone and S-(-)-alpha-phenylethylamine) and is well suited for a large scale, industrial process.

Description

technical field [0001] The present application relates to a process for the synthesis of 1-cyclopropylethyl-1-amines as building blocks for the preparation of substituted pyrazinones. These substituted pyrazinones can be used in the preparation of pharmaceutically active compounds containing substituted pyrazinone ring systems. Background technique [0002] Cyclopropylalkylamines can be prepared by methods known in the literature and converted to substituted pyrazinones by adapting methods known in the literature. These substituted pyrazinone compounds can then be used to prepare pharmaceutically active compounds containing a pyrazinone ring, such as RORγ modulators. These RORγ modulators are useful in the treatment of a variety of diseases and disorders mediated by this pathway. Diseases that may be treated include, but are not limited to, psoriasis and other inflammatory diseases. The preparation of RORγ modulators containing substituted pyrazinone rings is disclosed in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/28C07C211/08
CPCC07C209/28C07C211/08B01J23/44
Inventor 邓达杜占权K·格罗尔S·霍夫迪兹M·劳贝M·庞格尔C·林克肖青朱志斌
Owner BOEHRINGER INGELHEIM INT GMBH