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

GarciaMartinez Cirilo | Zendy; Hernandez Gilberto | Zendy; Biba Mirlinda | Zendy; Welch Christopher J. | Zendy

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

Author(s) -

GarciaMartinez Cirilo,

Hernandez Gilberto,

Biba Mirlinda,

Welch Christopher J.

Publication year - 2005

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.20154

Subject(s) - chemistry , enantiomer , optical rotation , diastereomer , chloroform , composition (language) , enantiomeric excess , chirality (physics) , nuclear magnetic resonance spectroscopy , analytical chemistry (journal) , stereochemistry , chromatography , organic chemistry , enantioselective synthesis , chiral symmetry , catalysis , linguistics , philosophy , nambu–jona lasinio model , physics , quantum mechanics , quark

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. Chirality 17:212–217, 2005. © 2005 Wiley‐Liss, Inc.

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