Water → trans-{4-(Benzyl-methyl-amino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-yl}-methanol

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Reaction Steps

A solution of trans-4-(benzyl-methyl-amino)-1-[2-(4-fluorophenyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester (144 mg, 361 μmol) in tetrahydrofuran (1 mL) was treated with a solution of lithium aluminum hydride (1.0 M in tetrahydrofuran, 723 μL, 723 μmol). The mixture was stirred at room temperature for 2.5 hours, then was treated very slowly with 28 μL of water, followed by 28 μL of 15% aqueous sodium hydroxide, then by 84 μL of water. The mixture was filtered and the solid was washed with ether. The filtrate and washes were combined and concentrated under vacuum to provide a white solid (116 mg, 90%). 1H NMR (300 MHz, CDCl3) δ7.34 (m, 5H), 7.15 (m, 2H), 6.98 (t, J=9 Hz, 2H), 6.26 (bs, 1H), 3.78 (d, J=13 Hz, 1H), 3.60 (m, 2H), 3.50 (m, 1H), 3.10 (m, 1H), 2.87 (m, 1H), 2.78 (m, 2H), 2.54 (m, 2H), 2.28 (s, 3H), 2.20 (m, 1H), 1.88 (m, 2H), 1.75 (m, 1H), 1.58 (m, 1H). Mass spec (ES+) m/z 357.3 (M+H+).

Provenance & Evidence