Enantioseparation of 3-substituted isoindolin-1-ones by HPLC

The enantioseparation of 3-alkyl-isoindolin-1-ones(1—9) and 3-alkyl-3-hydroxy-isoindolin-1-ones(10—14)(R=Me,Et,n-Pr,n-Bu,n-C_5H_ 11 ,n-C_7H_ 15 ,i-Bu,Ph and Bn),as well as 3-n-heptyl-2-[2-hydroxy-1-phenylethyl]-isoindolin-1-one(15) by HPLC using (S)-tert-leucine and (S)-1-α-NEA as a chiral stationary phase,and 1%—6%(volume fraction) 2-propanol or ethanol in hexane as the mobile phase was studied. The effect of content of polar solvent in mobile phase on the enantioseparation was discussed. The effects of 3-substituents on retention factor and chiral recognition were studied. For the majority of racemates(1—14),a baseline separation could be obtained. For racemate(15),the elution orders are (3R,1′R)/(3S,1′S) then (3R,1′S)/(3S,1′R) with n-hexane/2-propanol(volume ratio 99∶1) as a mobile phase and the resolutions are 1.44 and 5.58,respectively. [WT5HZ]