3-[4-(Benzyloxy)phenoxy]quinuclidine → 4-(1-Azabicyclo[2.2.2]oct-3-yloxy)phenol

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Reaction Steps

The product of Example 15A (1.20 g, 3.9 mmol) in ethanol (20 mL) was treated with Pd/C (Aldrich, 10% wt., 0.2 g) under H2 at ambient temperature for 10 hours. The mixture filtered through a short column of diatomaceous earth and the filtrate was concentrated under reduced pressure to provide the title compound as a colorless oil (0.72, yield, 84%). 1H NMR (MeOH-d4, 300 MHz) δ 1.40–1.56 (m, 1H), 1.64–1.75 (m, 1H), 1.80–1.92 (m, 1H), 2.00–2.30 (m, 2H), 2.76–3.02 (m, 5H), 3.25–3.35 (m, 1H), 4.40 (m, 1H), 6.60–6.80 (m, 4H) ppm. MS (DCl/NH3) m/z 220 (M+H) +.

Provenance & Evidence