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Syntheses and proton nmr spectroscopic investigations of some pyrrolidine carboxylic acids designed as potential glial gamma amino butyric acid uptake inhibitors



Syntheses and proton nmr spectroscopic investigations of some pyrrolidine carboxylic acids designed as potential glial gamma amino butyric acid uptake inhibitors



Acta Chemica Scandinavica Series B Organic Chemistry & Biochemistry 35(7): 473-480



The syntheses of 3-pyrroline-3-carboxylic acid (5), cis-4-hydroxypyrrolidine-3-carboxylic acid (6), 3-hydroxyoyrrolidine-3-carboxylic acid (11), pyrrolidine-3-acetic acid (homo-.beta.-proline) and cis-4-aminopyrrolidine-3-carboxylic acid (20) are described. Catalytic hydrogenation of appropriate cyclic .beta.-oxoesters are keysteps in the preparation of 5 and 6. Compound 11 was synthesized from the ketone via the corresponding protected cyanohydrin, and homo-.beta.-proline was prepared via a Knoevenagel reaction. The .beta.-amino acid 20 was prepared by stepwise hydrogenation of the enamine followed by acid treatment of the protected product. 1H-NMR spectroscopic analyses (270 MHz) were carried out to establish the relative stereochemistry of 6 and 20.

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