Sodium Hydroxide → 4-[5-(4-Fluoro-Phenyl)-4-Methoxymethyl-Oxazol-2-yl]-Piperidine

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Reaction Steps

A solution of 1-{4-[5-(4-fluoro-phenyl)-4-methoxymethyl-oxazol-2-yl]-piperidin-1-yl}-ethanone (0.79 g; 2.38 mmol) in ethanol (8 ml) is treated with a solution of sodium hydroxide (1.9 g; 47.59 mmol) in water (4 ml) and heated to 75 C. for 16 hours. Ethanol is removed in a rotary evaporator and the residue partitioned between ethyl acetate (100 ml) and water (20 ml). The aqueous phase is washed with ethyl acetate (2×30 ml) and chloroform (2×30 ml). The organic phases are washed with saturated brine (10 ml), dried over sodium sulfate and concentrated to dryness to afford the product as a yellow oil (0.55 g; 80%) which was used without further purification. HNMR (CDCl3): 7.53 (m, 2H), 7.02 (t, 2H, J=8.6 Hz), 4.36 (s, 2H), 3.36 (s, 3H), 3.06 (m, 2H), 2.85 (ttt, 1H, J=11.3; 3.9 Hz), 2.63 (m, 2H), 1.98 (m, 2H), 1.71 (m, 2H).

Provenance & Evidence