4-Cyclohexylbenzenamine → Methyl 5-[(4-cyclohexylphenyl)amino]-5,6,7,8-tetrahydronaphthalene-2-carboxylate

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Reaction Steps

A mixture of methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (1.2 g, 5.9 mmol), 4-cyclohexylaniline (2.1 g, 11.8 mmol), decaborane (0.22 g, 1.8 mmol) in dry MeOH (20 mL) was stirred under nitrogen for 4 h. Solvent evaporation and chromatography (5% to 20% EtOAc in Hexane) gave methyl 5-[(4-cyclohexylphenyl)amino]-5,6,7,8-tetrahydronaphthalene-2-carboxylate as a yellow solid. HPLC/MS: m/z=364.2 (M+1), Rt=2.83 min. 1H NMR (CDCl3): δ 7.86 (1H, s), 7.85 (1H, d, J=7.5 Hz), 7.54 (1H, d, J=7.5 Hz), 7.11 (2H, d, J=8.5 Hz), 6.68 (2H, d, J=8.5 Hz), 4.66 (1H, t, J=5.5 Hz), 3.96 (3H, s), 3.79 (1H, br s), 2.97-2.82 (2H, m), 2.46 (1H, m), 2.10-1.78 (9H, m), 1.44 (4H, m), 1.30 (1H, m).

Provenance & Evidence