3-(4-Nitrophenoxy)quinuclidine → 4-(1-Azabicyclo[2.2.2]oct-3-yloxy)aniline

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Reaction Steps

The product of Example 22A (1.02 g, 4.1 mmol) in MeOH (25 mL) was treated with Pd/C (Aldrich, 10%, 150 mg) under H2 at room temperature for 1.5 hours. The mixture was filtered through a short column of diatomaceous earth and the filtrate was concentrated under reduced pressure to provide the title compound (0.92 g, yield, 100%). 1H NMR (MeOH-d4, 300 MHz) δ 1.40–1.56 (m, 1H), 1.65–1.90 (m, 2H), 1.96–2.13 (m, 2H), 2.70–3.00 (m, 5H), 3.10–3.20 (m, 1H), 4.35 (m, 1H), 6.65–6.78 (m, 4H) ppm. MS (DCl/NH3) m/z 219 (M+1)+.

Provenance & Evidence