Resolution of amines
AssigneeLaboratorios Del Dr. Esteve, S.A.
InventorsAntoni Torrens-Jover, Jordi Frigola-Constansa
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Abstract
The procedure comprises reacting the mixture that comprises 2-[phenyl(1-methyl-1 H-pyrazole-5-yl)methoxy]-N,N-dimethylethanamine (I) with an enantiomer of an optically active acid to form a diastereoisomeric salt, separating said salt and liberating the enantiomer of said compound (I). The dextrorotatory enantiomer of (I) can be obtained by reacting a racemic mixture or non-racemic mixture of (I) with (+)-ditoluyl-L-tartaric acid, optionally mixed with p-toluensulphonic acid. Compound (I) has analgesic properties and its most active enantiomer is dextrorotatory.
Claims16
A process for resolving 2-[phenyl(1-methyl-1 H-pyrazole-5-yl)methoxy]-N,N-dimethylethanamine of formula I
- into its enantiomers comprising the steps of:
- a) reacting 2-[phenyl(1-methyl-1 H-pyrazole-5-yl)methoxy]-N,N-dimethylethanamine with an optically active acid selected from (+)-ditoluyl-L-tartaric acid, (−)-ditoluyl-L-tartaric acid or a mixture thereof in a solvent to form a diastereoisomeric salt between one of the enantiomers of formula (I) and one of (+)ditoluyl-L-tartaric acid or (−)ditoluyl-L-tartaric acid;
- b) separating the diastereoisomeric salt and
- c) isolating the enantiomer of 2-[phenyl(1-methyl-1-pyrazole-5-yl)methoxy]-N,N-dimethylethanamine.
Dependencies are inferred from the claim text.