Determination of enantiomeric composition of (-)-(R)-2-tert-butyltetrahydroimidazolidin-4-one by polarimetry, 1H NMR, and chiral SFC

Partial resolution of rac-2-tert-butyltetrahydroimidazolidin-4-one was carried out by recrystallization of diastereomeric salts. The enantiomeric composition of enriched samples was estimated by polarimetry, (1)H NMR, and chiral SFC. Enantiomeric composition estimated by polarimetry or by (1)H NMR was directly proportional to that estimated by chiral SFC. The occurrence of solute self-association in chloroform was detected through measurements of optical and specific rotation at variable concentration of (-)-(R)-2-tert-butyltetrahydroimidazolidin-4-one. Our data suggest that solute self-association in chloroform might be independent of enantiomeric composition.