Ethyl 1-benzoylpiperidine-4-carboxylate → 4-Piperidinemethanol, 1-benzoyl-

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Reaction Steps

A solution of lithium borohydride in tetrahydrofuran (2 M, 0.95 mL, 1.9 mmol) was added dropwise to a solution of ethyl 1-benzoylpiperidine-4-carboxylate (1 g, 3.8 mmol) in tetrahydrofuran (10 mL) with stirring under a nitrogen atmosphere. The reaction mixture was stirred for 18 h, poured onto water and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Column chromatography (ethylacetate) afforded 1-benzoyl-4-hydroxymethylpiperidine, a solid (522 mg, Rf =0.14): m.p. 85°-87° C.; 'H-NMR (CDCl3, 200 MHz): 7.45-7.35 (m, 5H), 4.8-4.6 (m, 1H), 3.9-3.7 (m, 1H), 3.5 (br s, 2H), 3.2-3.6 (m, 3H), 2.25 (br s, 1H), 2.0-1.6 (m, 3H), 1.4-1.0 (m, 2H); HRMS: Calcd. for C13H17NO2 :219.1259; Found: 19.1245.

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