METHOD FOR PRODUCING 5-AMINOSPIRO [2.3] HEXANE-1-CARBOXYLIC ACID Russian patent published in 2018 - IPC C07C227/18 C07C229/46 

FIELD: chemistry.

SUBSTANCE: invention relates to a process for production of 5-amino-spiro[2.3]hexane-1-carboxylic acid of the following formula. Process is characterized in that in the 3-(methylene) cyclobutane carboxylic acid, using a modified Curtius reaction, the carboxyl group is transformed into an amino group protected by a Boc fragment. Further, the diazoacetic ester and the obtained tert-butyl ester N-(3-methylenecyclobutyl) carbamic acid taken in the ratio 1:1.2-2 are reacted in the presence of 1-10 mole% of tetraacetate with formation of N-[1-(ethoxycarbonyl)spiro[2.3]hex-5-yl] carbamic acid tert-butyl ester. Then the subsequent removal of Boc group by 3-6 N hydrogen chloride solution in diethyl ether and hydrolysis by 2-5-fold excess of 1 N aqueous sodium hydroxide solution lead to 5-amino-spiro[2.3]hexane-1-carboxylic acid. .

EFFECT: proposed method makes it possible to obtain 5-amino-spiro[2.3]hexane-1-carboxylic acid, which extends the range of synthetic analogs of γ-aminobutyric acid with limited conformational mobility, which can be used in pharmaceutical and medical chemistry as physiologically active compounds.

1 cl, 2 ex