Potassium tert-butoxide → tert-Butyl 4-(((4'-cyano-5-(trifluoromethyl)biphenyl-3-yl)methoxy)methyl)-4-(pyridin-4-yl)piperidine-1-carboxylate

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A flask was charged with 3′-(bromomethyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (157 mg, 0.462 mmol) and tert-butyl 4-(hydroxymethyl)-4-(pyridin-4-yl)piperidine-1-carboxylate (90 mg, 0.308 mmol) in tetrahydrofuran (10 mL) at 0° C. The reaction was treated with potassium tert-butoxide (34.6 mg, 0.308 mmol), stirred at 0° C. for 20 min, and treated with another aliquot of potassium tert-butoxide (34.6 mg, 0.308 mmol). The reaction was allowed to warm to room temperature for 30 min, then diluted with 10% sodium bicarbonate, and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with brine (1×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (0%→65% ethyl acetate/hexanes) gave 50 mg (29%). Mass spec.: 552.18 (MH)+ LC tr=2.54 min (HPLC Method 1).

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