Sodium Hydroxide → tert-Butyl 4-(hydroxymethyl)-4-(pyridin-4-yl)piperidine-1-carboxylate

Participants

Reaction Steps

A flask was charged with 1-tert-butyl 4-ethyl 4-(pyridin-4-yl)piperidine-1,4-dicarboxylate (250 mg, 0.748 mmol) in tetrahydrofuran (3 mL) and cooled to −50° C. (acetonitrile/dry ice). Lithium aluminum hydride (0.785 ml, 1.570 mmol) was added dropwise, and the reaction was allowed to stir for 30 min. The flask was then warmed to room temperature and slowly diluted with ethyl acetate (5 mL). Water (61 μL) was added and the reaction allowed to stir for 5 min. Sodium Hydroxide (1 N in water, 120 μL) was then added and the reaction allowed to stir for 5 min. An additional portion of water (61 μL) and a small amount of sodium sulfate was added and the resulting mixture allowed to stir for 5 min. The suspension was filtered through celite, and the resulting pad washed with hot ethyl acetate. The filtrate was concentrated in vacuo to yield 90 mg (41%) of desired product. Mass Spec.: 294.05 (MH)+. LC tr=1.79 min (HPLC Method 1).

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