Methanesulfonyl chloride → 4-(1-(3-(Tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butyl methanesulfonate

Participants

Reaction Steps

MsCl (0.036 ml, 0.462 mmol) was added to a solution of 4-(1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2] octan-4-yl)butan-1-ol (111 mg, 0.31 mmol) and TEA (0.129 ml, 0.92 mmol) in DCM (2 mL) at 0° C. The reaction was then stirred at rt for 2 h and concentrated in vacuo. The residue was dissolved in EtOAc (5 mL), washed with water (4×5 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on SiO2 (gradient from 0 to 50% EtOAc: hexanes) to afford the title compound (133 mg, 98% yield) as a clear oil. 1H NMR (500 MHz, CDCl3) δ 7.23 (t, J=8.0 Hz, 1H), 7.13-7.10 (m, 1H), 7.03-6.99 (m, 1H), 6.94 (ddd, J=8.2, 2.5, 0.8 Hz, 1H), 5.44 (t, J=3.2 Hz, 1H), 4.25 (t, J=6.5 Hz, 2H), 4.04-3.88 (m, 1H), 3.82 (s, 2H), 3.67-3.55 (m, 1H), 3.03 (s, 3H), 2.06-1.99 (m, 5H), 1.90-1.83 (m, 2H), 1.79-1.57 (m, 9H), 1.43-1.34 (m, 2H), 1.23-1.16 (m, 2H).

Provenance & Evidence