(Pyridin-4-yl)boronic acid → (R)-3'-[4-(4-Pyridyl)thiophen-2-yl]spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one

Participants

Reaction Steps

The title compound was prepared by a method analogous to that described in Example 1 from (R)-3′-(4-bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one and pyridine-4-boronic acid. The solid obtained after flash chromatography was further purified by reverse phase HPLC on a Phenomenex® Polar RP column using a gradient of 5-45% acetonitrile/water (each solvent containing 0.1% trifluoroacetic acid as a buffer) as the eluant. The residue was partitioned between saturated aqueous potassium carbonate and chloroform and the chloroform layer was dried (magnesium sulfate), filtered and evaporated to give the title compound as a pale solid (74 mg), m/z 342 (MH+).

Provenance & Evidence