3 results about "Amino nitriles" patented technology

The application relates to an industrialized preparation method and application of high-purity alpha-amino nitrile. The application belongs to the technical field of fine chemical synthesis. The purpose of the application is to solve the technical problems of low yield and purity, high cost and unsuitability for industrialized production of the existing alpha-amino nitrile synthesis method. The method of the application is as follows: taking imine as a substrate, alpha-amino nitrile is synthesized by reacting with acetone cyanohydrin under the action of an ionic liquid. The method of the application synthesizes a nucleophilic addition cyanyl product of a carbon-nitrogen double bond in one step at room temperature. By selecting the ionic liquid and reasonably controlling the proportioning of various substances, the reaction process is greatly accelerated, the high-efficiency synthesis of alpha-amino nitrile is realized, the purity of alpha-amino nitrile is remarkably improved, the substrate adaptability is good, and the method can be widely applied to the synthesis in the fields of medicines and the like in the industry and the academia.

This invention provides a method for synthesizing milobalin benzylsulfonic acid, comprising the following steps: a chiral enone undergoes a condensation reaction with cyanoacetate in the presence of ammonium acetate to obtain an unsaturated cyano ester; next, the unsaturated cyano ester undergoes a condensation reaction with nitromethane to obtain a nitro ester; the nitro ester is then deesterified at high temperature to obtain a chiral nitro nitrile, which is then reduced to a chiral amino nitrile; subsequently, the chiral amino nitrile is hydrolyzed to obtain the free base of milobalin; finally, the free base of milobalin is salted with benzylsulfonic acid to obtain milobalin benzylsulfonic acid. This invention stereospecifically constructs a chiral cyclobutane quaternary carbon center to obtain a chiral nitro ester with a single stereoconfiguration, avoiding the chiral isomer waste generated by chiral isomer resolution, eliminating the need for chiral column separation or chiral resolution, significantly reducing production costs, and simultaneously avoiding the environmental pollution caused by residual heavy metal titanium in the product and solid waste heavy metal titanium.

The application belongs to the technical field of organic synthesis, and particularly relates to an amino nitrile compound with a remote chiral center and a preparation method and application thereof. The nickel-hydrogen catalytic asymmetric hydrogenation reaction provided by the application is realized through non-covalent pi-pi interaction between a cyano group in an olefin substrate and a chiral bisoxazoline ligand. The method not only realizes efficient and high-selectivity conversion of various olefin substrates and amine electrophilic reagents, but also is compatible with secondary alkyl amine electrophilic reagents, amide electrophilic reagents and benzisoxazole electrophilic reagents, thereby providing a reliable way for synthesizing chiral amino nitrile compounds (formula I) with a remote (beta-, gamma- and delta-) stereogenic center and various structures.