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Abstract
Abstract The discovery and selective synthesis of a novel and highly potent serotonin-3 receptor ligand, 4-amino-5-chloro-2-methoxy-N-(1-azabicyclo[2.2.2]-oct-2-enyl-2-methyl) benzamide (4) are described. The key step in the preparation of 4 involves an unusual example of a kinetically controlled displacement to provide a thermodynamically disfavored allytic azide isomer. This azide is a precursor to 2-aminomethyl-1-azabicylo[2.2.2]oct-2-ene (5), a convergent intermediate for the synthesis of analogs related to 4.
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