Journal article
Preparation and structural analysis of (±)-threo-ritalinic acid.
- Wyss S Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, Wolfgang-Pauli Strasse 10, Zurich 8093, Switzerland.
- Werner IA
- Schweizer WB
- Ametamey SM
- Milicevic Sephton S
- 2013-11-07
Published in:
- Acta crystallographica. Section C, Crystal structure communications. - 2013
(±)-threo-methyl phenidate
(±)-threo-ritalinic acid
Ritalin®
crystal structure
gauche+–gauche- interactions
hydrolysis
Crystallography, X-Ray
Hydrogen Bonding
Magnetic Resonance Spectroscopy
Methylphenidate
Molecular Structure
Stereoisomerism
English
Hydrolysis of the methyl ester (±)-threo-methyl phenidate afforded the free acid in 40% yield, viz. (±)-threo-ritalinic acid, C13H17NO2. Hydrolysis and subsequent crystallization were accomplished at pH values between 5 and 7 to yield colourless prisms which were analysed by X-ray crystallography. Crystals of (±)-threo-ritalinic acid belong to the P21/n space group and form intermolecular hydrogen bonds. An antiperiplanar disposition of the H atoms of the (HOOC-)CH-CHpy group (py is pyridine) was found in both the solid (diffraction analysis) and solution state (NMR analysis). It was also determined that (±)-threo-ritalinic acid conforms to the minimization of negative gauche(+)-gauche(-) interactions.
- Language
-
- English
- Open access status
- closed
- Identifiers
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- DOI 10.1107/S010827011302595X
- PMID 24192163
- Persistent URL
- https://sonar.ch/global/documents/180637
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