1-Aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochloride → [1R,3S] 1-aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride

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Reaction Steps

To 0.22 g (0.73 mmol) of 1-aminomethyl-5-methoxy-3-phenyl-3,4-dihydronaphthalene hydrochloride, from Step 2, of Example 2, in 5 mL of absolute ethanol, was added 0.05 g of 10% palladium supported on carbon. The reaction mixture was sealed under a blanket of hydrogen and stirred overnight at ambient temperature. The reaction mixture was flushed with nitrogen before it was filtered through Celite filter aid and washed with 15 mL of absolute ethanol and 15 mL of methylene chloride. The filtrate was concentrated to give 0.16 g (79% yield) of [1R,3S] 1-aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride, m. p. 235°-237° C.; 1H NMR (d6-DMSO) δ2.15-2.25 (m, 2H), 2.5-2.65 (m, 1H), 2.8-2.95 (m, 2H), 3.0-3.1 (m, 1H), 3.1-3.4 (m, 1H), 3.45-3.5 (m, 1H), 3.72 (s, 3H), 6.43 (d, 1H), 6.62 (d, 1H), 6.94 (t, 1H), 7.2-7.3 (m, 1H), 7.35-7.45 (m, 4H).

Provenance & Evidence