(+-)-3-Quinuclidinol → HCID 11347518, compound

Participants

Reaction Steps

3-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) was treated with 4-(4-fluoro-phenoxy)-phenol (Aldrich, 205 mg, 1 mmol) according to the procedure of Example 1A. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.45) as oil (230 mg, yield, 73%). 1H NMR (MeOH-d4, 300 MHz) δ 1.40–1.52 (m, 1H), 1.64–1.87 (m, 2H), 1.98–2.15 (m, 1H), 2.20–2.25 (m, 1H), 2.66–3.00 (m, 5H), 3.30–3.40 (m, 1H), 4.48(m, 1H), 6.61 (dt, J=10.5, 2.4 Hz, 1H), 6.71(dd, J=8.1, 2.3 Hz, 1H), 6.76 (tdd, J=8.4, 2.3, 1.0 Hz, 1H), 6.87–7.00 (m, 3H), 7.22–7.32 (m, 2H) ppm. MS (DCl/NH3) m/z 314 (M+H)+.

Provenance & Evidence