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Preparation of (+)‐ and (−)‐1,2‐dimethyl‐3‐pyrrolidone and stability studies
Author(s) -
Collina Simona,
Gamba Anna,
Ghislandi Victor,
Azzolina Ornella
Publication year - 1995
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.530070609
Subject(s) - chemistry , diastereomer , conformational isomerism , enantiomer , tautomer , nuclear magnetic resonance spectroscopy , tartaric acid , chirality (physics) , stereochemistry , computational chemistry , crystallography , organic chemistry , molecule , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , citric acid , quark
1,2‐Dimethyl‐3‐pyrrolidone is an important intermediate in the synthesis of cycloalkylaminonaphthalenic analgesics. The optical resolution of this compound with L‐ and D‐tartaric acids is described and the behaviour of the diastereomeric tartrates and of the enantiomers in solution was investigated by NMR spectroscopy and polarimetric analysis. Tautomeric equilibria involving C4 and C2 atoms, which are responsible for the instability of the compound, are demonstrated. Theoretical studies of conformational analysis were also made in order to define the relationships between the stability of the conformers of 1,2‐dimethyl‐3‐pyrrolidone and its structural features. © 1995 Wiley‐Liss, Inc.