Diisobutylaluminum hydride → HCID 90408708, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of 2-(1-(3-fluoro-5-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octan-4-yl) acetaldehyde (424 mg, 1.22 mmol) in DCM (5 mL) under N2 was added DIBAL-H (1.34 mL of a 1.0 M solution in DCM, 1.34 mmol) dropwise. The reaction mixture was stirred at −78° C. for 2 h; CELITE® (500 mg) was then added and the reaction was quenched with sat. aq. NH4Cl (0.5 mL). The mixture was stirred at rt for 30 min, MgSO4 (500 mg) was added, and the mixture was stirred at rt for 30 min. The mixture was filtered and the residual solid was washed with DCM (3×). The combined filtrates were concentrated in vacuo. The crude oil was purified by flash chromatography (SiO2) using a gradient of 0% to 50% EtOAc/hexane (10 min) to give the title compound (350 mg, 1.00 mmol, 82% yield) as a clear oil. 1H NMR (CDCl3) δ: 6.85 (t, J=1.7 Hz, 1H), 6.73 (ddd, J=10.1, 2.3, 1.5 Hz, 1H), 6.66 (dt, J=10.6, 2.3 Hz, 1H), 5.38 (t, J=3.1 Hz, 1H), 3.94-3.81 (m, 3H), 3.70 (td, J=7.2, 4.1 Hz, 2H), 3.60 (dtd, J=11.3, 4.0, 1.2 Hz, 1H), 2.04-1.92 (m, 5H), 1.90-1.77 (m, 2H), 1.76-1.52 (m, 8H), 1.45 (t, J=7.3 Hz, 2H); 19F NMR (CDCl3) δ: −112.1 (s).

Provenance & Evidence