5-Fluoro-1-(piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one → (S)-2-{3-[4-(5-Fluoro-2-oxo-2,3-dihydro-benzoimidazol-1-yl)piperidin-1-yl]-2-hydroxy-propoxy}-benzoic acid tert-butyl ester

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Reaction Steps

A solution of 5-fluoro-1-piperidin-4-yl-1,3-dihydro-benzoimidazol-2-one (235 mg, 0.5 mmol) and 2-oxiranylmethoxy-benzoic acid tert-butyl ester (250 mg, 1.0 mmol) in isopropanol (iPrOH) (10 mL) was stirred at 70° C. for 14 h, after which the solvent was removed in vacuo. The residue was purified by gradient flash chromatography on silica gel (CH2Cl2 to EtOH), yielding an off-white solid (240 mg, 99%).

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