Imidazole → 7-{[Tert-butyl(dimethyl)silyl]oxy}-5,6,7,8-tetrahydronaphthalen-1-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-amino-2-naphthol (47.55 g, 298.7 mmol), Raney nickel (20.20 g), and 50% aq. NaOH (1.97 g) in ethanol (480 mL) in a sealed reactor was purged three times (3×40 psi H2/vacuum cycles), then the reactor was pressurized with 1300 psi H2 and heated at 85° C. for 7 hours. After this time, the catalyst was filtered off (Celite), and the filtrate was evaporated to afford a dark oil. The oil was dissolved in CH2Cl2 (600 mL) and was treated with imidazole (65.9 g, 969 mmol) and tert-butylchlorodimethylsilane (59.0 g, 392 mmol). The reaction mixture was stirred at room temperature for 18 hours, and washed with water and brine. The organic solution was dried over Na2SO4 and evaporated. The residue was chromatographed on silica gel (9:1 to 4:1 hexane-ethyl acetate, eluant) to afford the title compound as a dark purple oil, 44.22 g (49%). 1H NMR (300 MHz, DMSO-d6) δ 6.76 (m, 1H), 6.40 (m, 1H), 6.27 (d, J=7.5 Hz, 1H), 4.68 (br, 2H), 4.07 (m, 1H), 2.57-2.79 (m, 3H), 2.22 (m, 1H), 1.81 (m, 1H), 1.58 (m, 1H), 0.87 (s, 9H), 0.08 (s, 6H). MS (ESI+) m/z 278 (M+H)+.

Provenance & Evidence