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Synthesis of d-pilocarpine-N-14CH3
Abstract:
The total synthesis of d-pilocarpine specifically labeled as N-14CH3 is reported. dl-Homopilopic acid was prepared as a key intermediate and resolved into the d-enantiomer via the alpha-methylbenzylamine salt. The penultimate intermediate, 2-mercaptopilocarpine, was desulfurized by oxidation with dilute hydrogen peroxide, minimizing isomerization to isopilocarpine. Procedures for the analysis of pilocarpine-isopilocarpine mixtures by high-pressure liquid chromatography are also described.
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