Water → 2-Dimethylaminomethyl-3-(3-methoxy-phenyl)-bicyclo[3.2.1]octan-3-ol hydrochloride

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Reaction Steps

Add H2O (100 mg, 5.56 mmol) and TMSCl (361 mg, 3.34 mmol) to a solution of 2-dimethylaminomethyl-3-(3-methoxy-phenyl)-bicyclo[3.2.1]octan-3-ol (877 mg, 3.03 mmol) in 2-butanone (60 mL). Stir the mixture at ambient temperature for 12 hours. Concentrate the mixture under vacuum to give 2-dimethylaminomethyl-3-(3-methoxy-phenyl)-bicyclo[3.2.1]octan-3-ol hydrochloride as white solid (986 mg, Yield: 100%). 1H NMR (400 MHz, D2O) δ 7.23-7.27 (t, J=16.4, 1H), 7.00-7.02 (d, J=8.0, 1H), 6.95-6.96 (t, J=4.0, 1H), 6.78-6.80 (d, J=10.4, 1H), 3.71 (s, 3H), 3.05-3.19 (m, 1H), 2.52-2.58 (m, 4H), 2.14-2.26 (m, 4H), 2.09-2.14 (m, 2H), 2.05-2.06 (d, J=2.4, 1H), 1.89-1.92 (m, 1H), 1.78-1.80 (m, 1H), 1.51-1.68 (m, 4H), 1.40-1.52 (m, 1H).

Provenance & Evidence