Enantioseparation of 3-Substituted Isoindolin-1-ones by HPLC

Abstract

Abstract: 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-C₅H₁₁ ,n-C₇H₁₅ ,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.

Key words: 3-Substituted isoindolin-1-one, Enantioseparation, High performance liquid chromatography(HPLC), Chiral stationary phase

CLC Number:

O657.7

TrendMD:

RUAN Yuan-Ping, XU Xiu-Qing, HE Ming-Zhu, ZHOU Xiang, HUANG Pei-Qiang. Enantioseparation of 3-Substituted Isoindolin-1-ones by HPLC[J]. Chem. J. Chinese Universities, 2004, 25(6): 1031.

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Enantioseparation of 3-Substituted Isoindolin-1-ones by HPLC

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