To a solution of tert-butyl 4-(4-(ethoxycarbonyl)phenoxy)piperidine-1-carboxylate (500 mg, 1.43 mmol) in tetrahydrofuran (THF, 10 mL) was slowly added lithium aluminum hydride (LiAlH4, 0.16 g, 4.29 mmol) at 0 °C. The temperature was maintained and the reaction mixture was stirred continuously for 30 min. Subsequently, 1 M aqueous sodium hydroxide (NaOH) solution (10 mL) was added to the reaction system to form a two-phase mixture. The reaction mixture was extracted with dichloromethane (DCM, 3 x 50 mL). The organic phases were combined and washed with saturated sodium chloride (NaCl) aqueous solution (2 × 50 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford the target product tert-butyl 4-(4-(hydroxymethyl)phenoxy)piperidine-1-carboxylate (350 mg, 1.14 mmol) as a colorless oil.
