2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol → 3-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanenitrile

3-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanenitrile was prepared using a procedure analogous to 5-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)pentanenitrile except that 4-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butan-1-ol was replaced with 2-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol. The title compound was obtained (490 mg, 1.435 mmol, 87% yield) as a white solid. LCMS, [M+NH4]+=359.2. 1H NMR (500 MHz, CDCl3) δ 7.24 (t, J=8.0 Hz, 1H), 7.14-7.10 (m, 1H), 7.03-6.99 (m, 1H), 6.96 (ddd, J=8.2, 2.5, 0.8 Hz, 1H), 5.45 (t, J=3.2 Hz, 1H), 3.94 (ddd, J=11.3, 9.7, 3.2 Hz, 1H), 3.85 (s, 2H), 3.62 (m, 1H), 2.36-2.30 (m, 2H), 2.11-1.98 (m, 5H), 1.90-1.84 (m, 2H), 1.77-1.59 (m, 9H).