PURPOSE: To obtain a compound useful as an intermediate for pharmaceuticals from a versatile raw material with a few steps.
CONSTITUTION: This bicyclohexanamine derivative expressed by formula I (R3 is a 1-20C alkyl, etc., an aralkyl, etc.; R5 is an alkoxycarbonyl) is produced by reacting an olefin of formula II (R1 is a hydroxyl-protecting group) with a diazoacetic acid ester of formula N2CHCOOR2 (R2 is a 1-20C alkyl, etc.) in the presence of 0.01-5mol% (based on the ester) of a catalyst such as copper chloride, deprotecting the obtained cyclopropane compound to form a hydroxycyclopropane compound, halogenating the product, subjecting the obtained halogenocyclopropane compound to cyclization reaction with a primary amine of formula N2N-R2 to form a bicycloaminoester compound, hydrolyzing the ester and finally converting the carboxylic acid part of the obtained bicycloamino acid compound of formula III into an amine by rearrangement.
MIYAMOTO YASUNOBU
TAKAHATA TETSUHIKO
Next Patent: 1,2,5,6-TETRAHYDROPYRIDIN-2-ONE DERIVATIVE AND HERBICIDE