1-Aminomethyl-3-cyclohexyl-5,6-dimethoxy-3,4-dihydronaphthalene hydrochloride → [1R,3S]1-Aminomethyl-3-cyclohexyl-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalene Hydrochloride

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Reaction Steps

1-Aminomethyl-3-cyclohexyl-5,6-dimethoxy-3,4-dihydronaphthalene hydrochloride (1 g, 3.3 mmol), from Step 2 of Example 36, was dissolved in 20 mL of ethanol and 0.25 g of 10% palladium on carbon was added to the ethanol solution. The reaction mixture was sealed under one atmosphere of hydrogen and shaken at ambient temperature for 24 h. The reaction mixture was filtered to remove the catalyst and concentrated to give 1 g (100% yield) of the title compound, m.p. 282°-283° C.; 1H NMR (d6 -DMSO) δ: 1.0-1.5 (m, 8H), 1.5-1.9 (m, 5H), 2.0-2.2 (m, 2H), 2.7-3.1 (m, 3H), 3.3-3.4 (m, 1H), 3.8 (s, 3H), 3.9 (s, 3H), 6.4-6.8 (m, 2H).

Provenance & Evidence