Synthesis Of 2,2,3,3-Tetramethylcyclopropylmethylamine And It's Derivatives

2,2,3,3-Tetramethylcyclopropylcarboxylic acid due to its good biological activity,is widely used as key intermediates in sythesis of pyrethroid pesticides,and new plant growth regulator,acute pain medications,Fluoroquinolones.In recent years,its derivatives of amide in the treatment of epilepsy,such as the anticonvulsant physiological role is constantly being reported.As the derivatives(2,2,3,3-tetramethylcyclopropanecarboxamide,2,2,3,3-Tetramethylcyclopropylmethylamine,etc)were the key intermediates,how to manufacture them in high purity and low price by 2,2,3,3-tetramethylcyclopropylcarboxylic acid was very valuable.In this paper,the 2,2,3,3-tetramethylcyclopropylcarboxylic acid derivatives,namely 2,2,3,3-tetramethylcyclopropanecarboxamide,2,2,3,3-tetramethylcyclopropylmethylamine, N-(methyl)-2,2,3,3-tetrarnethylcyclopropanecarboxamide,N,N-(Dimethyl)-2,2,3,3-tetra-methylcyclopropanecarboxamide were prepared;N-(n-Bu)- 2,2,3,3-tetramethylcyclopropane-carboxamide,N-(4-methylphenyl)-2,2,3,3-tetramethylcyclopr-opanecarboxamide, N-(3-nitro-phenyl)-2,2,3,3-tetramethylcyclopropanecarboxamide,ect.were firstly synthesized by using thionyl chloride in Dimethylacetamide in the Absence of Bases.2,2,3,3-tetramethyl-cyclopropylmethylamine,N-(methyl)-2,2,3,3-tetramethylcyclopropylm ethylamine,N,N-(Di-methyl)-2,2,3,3-tetramethylcyclopropylmethylamine,N-(n-Bu)-2,2,3,3-tetramethylcyclo-propylmethylamine and N-(phenyl)-2,2,3,3-tetramethylcyclopropyl-methylamine were firstly prepared separately by using lithium aluminum hydride,sodium borohydride / titanium tetrachloride and sodium borohydride / aluminum chloride system as reducing agent.It found that 2,2,3,3- tetramethylcyclopropylmethylamine can be sythesised separately by using sodium borohydride / titanium tetrachloride system and sodium borohydride / aluminum chloride system as reducing agent.The effects of ratios of reactants,reaction time, reaction temperature,dosage of promoter and different solvents on the reducing reaction were investigated thoroughly.The optimal reactive conditions were obtained on the basis of above investigation.