Process for preparing cyclobutane-1,2-dicarboxylic esters

Details Process for preparing cyclobutane-1,2-dicarboxylic esters Process for preparing cyclobutane-1,2-dicarboxylic esters

C - Chemistry, Metallurgy

07

C

C07C 69/757 (2006.01) C07C 67/347 (2006.01) C07C 67/46 (2006.01) C07D 307/20 (2006.01) C07D 309/12 (2006.01) C07D 317/72 (2006.01) C07D 319/08 (2006.01) C07D 321/10 (2006.01) C07D 407/14 (2006.01)

Patent

CA 2242218

Cyclobutane-1,2-dicarboxylic esters of the formula: (see formula I) in which R1 is a Cl-8-alkyl group, an optionally substituted mono- or bicyclic cycloaliphatic group having 3 to 10 ring carbon atoms, an optionally substituted aryl or arylalkyl group or an optionally substituted saturated heterocyclic group and R2 is either C1-4-alkyl or both radicals R2 together form a group of the formula -(CH2)n- (n = 2 to 4), are prepared from the corresponding maleic or fumaric ester and ketene acetal in the presence of a Lewis acid and a sterically hindered base. The reaction is stereoselective when an optically active maleic or fumaric ester is employed. The cyclobutane-1,2-dicarboxylic esters (I), in particular those having trans configuration, are intermediates in the synthesis of pharmaceutically active compounds.

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