Sodium borohydride → 4-[[5-(4-Hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoic acid

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Reaction Steps

To a solution of 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)-benzoyl]amino]benzoic acid (69.5 mg, 182.68 μmoles) in methanol (1.83 ml) is added sodium tetrahydroborate (13.82 mg, 365.36 μmoles) and the resulting mixture is stirred at ambient temperature. After 1 hour, the mixture is quenched with saturated solution of NH4Cl (0.2 ml) and extracted with CHCl3 (3 ml):IPA (1 ml). The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting solid is triturated with H2O (5 ml), filtered, and washed with H2O (5 ml). The residue is purified by reverse phase chromatography (C18) using 20% acetonitrile in H2O with 0.1% formic acid to afford the title compound as a white powder (0.01 g, 15.7%). Mass spectrum (m/z): 383.2 (M+1).

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