Hydrochloric Acid → 4-((3-(5-Methyl-1H-tetrazol-1-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine

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tert-Butyl 4-((3-(5-methyl-1H-tetrazol-1-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (40.0 mg, 0.08 mmol) was dissolved in a minimum amount of ethyl acetate, followed by addition of 4 N hydrochloric acid (1.5 mL). The mixture was stirred under nitrogen for 1 h. After removing the solvents, the crude mixture was precipitated in diethyl ether and filtered to afford 30.0 mg (93%) as a white powder. 1H-NMR (CDCl3, 500 MHz) δ 7.58 (s, 1H), 7.53 (s, 1H), 7.31-7.35 (m, 3H), 7.22-7.26 (m, 1H), 7.08-7.11 (m, 2H), 4.49 (s, 2H), 3.43 (s, 2H), 2.86-2.90 (m, 2H), 2.71-2.75 (m, 2H), 2.52 (s, 3H), 2.17-2.20 (m, 2H), 1.84-1.87 (m, 2H). 13C-NMR (CDCl3, 126 MHz) δ 151.5, 143.9, 143.1, 134.5, 136.6 (q, J=33.6 Hz), 128.7, 128.3, 127.2, 126.3, 127.7, 125.1 (q, J=272.6 Hz), 120.4, 80.6, 71.3, 42.6, 41.9, 33.6, 33.3. Mass spec.: 432.22 (MH)+.

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