Aluminium lithium hydride → HCID 90408285, compound

Participants

Reaction Steps

To a solution of methyl 2-((1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl)cyclopropanecarboxylate (110 mg, 0.280 mmol) in THF (1 mL) at 0° C. was added LAH (0.280 ml, 0.280 mmol) dropwise. The reaction was stirred at rt for 3 h, added CELITE® (200 mg), cooled to −78° C., and then quenched with sat′d aqueous NH4Cl (0.5 mL). The mixture was stirred at rt for 30 min, added MgSO4 (200 mg), and stirred at rt for another 1 h. The mixture was filtered. The solid was washed with DCM. The combined filtrates were concentrated in vacuo and the residue was purified by flash chromatography on SiO2 (0 to 30% EtOAc:hexanes) to afford the title compound (101 mg, 99% yield) as a clear oil. LCMS, [M+NH4]+=382.2. 1H NMR (500 MHz, CDCl3) δ 7.34-7.24 (m, 3H), 7.16-7.10 (m, 2H), 7.09-7.05 (m, 1H), 7.00-6.96 (m, 2H), 6.85-6.81 (m, 1H), 3.87 (s, 2H), 3.55 (dd, J=11.0, 6.6 Hz, 1H), 3.41 (dd, J=11.0, 7.2 Hz, 1H), 2.05-1.99 (m, 4H), 1.76-1.69 (m, 4H), 1.14 (dd, J=6.9, 4.7 Hz, 2H), 0.84-0.76 (m, 1H), 0.62-0.54 (m, 1H), 0.45-0.39 (m, 1H), 0.28 (dt, J=8.3, 4.8 Hz, 1H).

Provenance & Evidence