Sodium hydride → tert-Butyl 4-((2-methoxy-5-(2-methyl-2H-tetrazol-5-yl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

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5-(3-(Bromomethyl)-4-methoxyphenyl)-2-methyl-2H-tetrazole (35.0 mg, 0.12 mmol) and tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate (40.0 mg, 0.14 mmol) were combined in dimethylformamide (1 mL) and cooled to 0° C. The reaction was treated with sodium hydride (3.2 mg, 0.14 mmol), stirred at 0° C. for 1 h, and at room temperature overnight. The solvents were removed in vacuo and the crude product purified by column chromatography on silica gel (30% ethyl acetate/hexanes) to afford 30 mg (50%). LC/MS (HPLC method 3): tR=3.29 min, 494.25 (MH)+.

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