Methanol → 4-{4-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]phenoxy}phenol Fumarate

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Reaction Steps

The product of Example 9A (48 mg, 0.15 mmol) in ethyl acetate:MeOH (3 mL, 10:1) was treated with fumaric acid (Aldrich, 17.4 mg, 0.15 mmol) at room temperature and stirred overnight to provide the title compound as a solid (34 mg, yield, 62%). 1H NMR (MeOH-d4, 300 MHz) δ 1.73–2.19 (m, 3H), 2.21–2.40 (m, 1H), 2.41–2.56 (m, 1H), 3.03–3.27 (m, 5H), 3.59–3.73 (m, 1H), 4.67 (m, 1H), 6.67 (s, 1H), 6.67–6.98 (m, 8H) ppm. MS (DCl/NH3) m/z 312 (M+H)+. Anal. Calculated for C19H21NO3.0.5C4H4O4. 0.35H2O C, 67.13; H, 6.36; N, 3.73. Found: C, 67.04; H, 6.46; N, 3.75.

Provenance & Evidence