An expedient asymmetric synthesis
of TRPV1 antagonist 1 has been developed and demonstrated
on multikilogram scale. The enabling route to 1 is detailed
herein and characterized by the following key transformations: an
aldol-cyclodehydration sequence to install the chromanone, and an
auxiliary-mediated diastereoselective reductive amination.
The asymmetric unit of the title compound, 3C26H10Cl4N4S4·2C8H10, contains 1.5 quinoxaline molecules, one molecule having crystallographic inversion symmetry, and one para‐xylene solvent molecule. The solvent molecules lie in channels along the [010] direction of the unit cell.
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