3-[(4'-Nitro-1,1'-biphenyl-4-yl)oxy]quinuclidine → 4'-(1-Azabicyclo[2.2.2]oct-3-yloxy)-1,1'-biphenyl-4-amine

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Reaction Steps

The product of Example 15A (300 mg, 0.92 mmol) was treated with Pd/C (Aldrich, wt. 10%, 30 mg) in methanol (20 mL) under H2 at ambient temperature for 30 min. After the reaction was complete, the catalyst was removed through a short column of diatomaceous earth. The filtrate was concentrated under reduced pressure to provide the title compound (200 mg, yield, 74%). 1H NMR (300 MHz, CD3OD) δ 1.44–1.58 (m, 1H), 1.63–1.89 (m, 2H), 1.99–2.13 (m, 1H), 2.15–2.23 (m, 1H), 2.72–3.04 (m, 5H), 3.29–3.39 (m, 1H), 4.50–4.58 (m, 1H), 6.77 (dt, J=8.8, 2.5 Hz, 2H), 6.91 (dt, J=8.8, 2.4 Hz, 2H), 7.32 (dt, J=8.5, 2.5 Hz, 2H), 7.43 (dt, J=9.2, 2.8 Hz, 2H) ppm. MS (DCl/NH3) m/z 295 (M+H)+.

Provenance & Evidence