Patent ID: 6762316
Filing Date: 2004-07-13
Classification: C07C,C07D

Abstract:
A method for preparing a substituted cyclopentane compound represented by formulae 1a or 1b wherein each R1 individually is alkyl or substituted alkyl, alkenyl or substituted alkenyl of 1-6 carbon atoms, or H; each of R2 and R3 individually is alkyl or alkenyl of 1-8 carbon atoms, cycloalkyl or substituted cycloalkyl of 4-8 carbon atoms, aryl or substituted aryl, arylalkyl or substituted arylalkyl, or H provided at least one of R2 and R3 is other than H; X is NHR1, NHC(&boxH;NH)NHR4 where R4 is H, alkyl of 1-6 carbon atoms, OR1, COR1, COOR1, CN, or NO2; A is H, F, OR1, OCOR1, â€”OOCNHR1, NHR1, or NHCOOR1; andpharmaceutically acceptable salts thereof;which comprises:Step (1) obtaining an isoxazoline compound of formula 10; wherein each R1 individually is alkyl or substituted alkyl, alkenyl or substituted alkenyl of 1-6 carbon atoms; or H; each of R2 and R3 individually is alkyl or alkenyl of 1-8 carbon atoms; cycloalkyl or substituted cycloalkyl or 4-8 carbon atoms, aryl or substituted aryl, arylalkyl or substituted arylalkyl, or H provided at least one of R2 and R3 is other than H;which comprises reacting a nitrite oxide of formula 2 with a cyclopentane derivative having formula 9 to produce said isoxazoline compound; Step (2) converting said isoxazoline to a compound of formula 12 and dehydrating said compound of formula 12 to produce a compound of formula 13 or converting the OH groups of said compound of formula 12 to a group selected from F, OR1, OCOR1, NHR1 or NHCOOR1, except when said group is OR1, R1 is other than H.