A process for the preparation of alpha,alpha-difluoroproline

CN117843543BActive Publication Date: 2026-06-19NANJING TECH UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
NANJING TECH UNIV
Filing Date
2024-01-02
Publication Date
2026-06-19

AI Technical Summary

Technical Problem

Existing methods for synthesizing α,α-difluoropropiolactam are complex and have limited applicability of raw materials, necessitating the development of a more universal and efficient synthetic method.

Method used

Under a nitrogen atmosphere, difluorobromoacetylsilane compound, imine, and activator were added to the reaction solvent to prepare α,α-difluoropropiolactam via a [2+2] cycloaddition reaction. Potassium fluoride was used as the activator, and acetonitrile was used as the solvent. After the reaction, the mixture was separated by filtration and silica gel column chromatography.

Benefits of technology

A simple and efficient preparation of α,α-difluoropropiolactam has been achieved, avoiding the use of zinc and transition metal catalysts. It is applicable to a variety of imine structures, especially imine raw materials with large steric hindrance.

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Abstract

This invention relates to the field of organic synthesis and discloses a method for preparing α,α-difluorobutyrolactam. This method utilizes the [2+2] reaction of difluorobromosilylsilane with imine under the action of an activator to achieve the efficient preparation of α,α-difluorobutyrolactam. The method of this invention is simple to operate, operates under mild conditions, and has good substrate versatility, applicable to a series of imines derived from aldehydes, ketones, aliphatic amines, and aromatic amines, and is particularly suitable for the preparation of α,α-difluorobutyrolactams containing sterically hindered substituents.
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