Borane → (1-(4-Nitrophenyl)piperidin-4-yl)methanol

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Reaction Steps

To a 0° C. solution of 1-(4-nitrophenyl)piperidine-4-carboxylic acid (1.0 g, 4.0 mmol) in tetrahydrofuran (14 mL) is added borane.tetrahydrofuran complex (1.8 M, 7 mL, 13 mmol). After completion of the dropwise addition, the coolant is removed. The mixture is stirred overnight at room temperature and re-cooled to 0° C. in an ice-water bath. Sodium hydroxide solution (1M, 6 mL) is added dropwise. The basic mixture is neutralized by the addition of saturated aqueous ammonium chloride solution. The mixture is extracted 3× with ethyl acetate, and the combined extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give [1-(4-nitro-phenyl)-piperidin-4-yl]-methanol.

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