Aluminium lithium hydride → HCID 11293122, compound

Participants

Reaction Steps

{3-[1-(3-Benzyloxyphenyl)-8-chloroimidazo[1,5-a]pyrazin-3-yl]-phenyl}-methanol: To a solution of 3-[1-(3-benzyloxyphenyl)-8-chloroimidazo[1,5-a]pyrazin-3-yl]-benzoic acid methyl ester (552 mg, 1.17 mmol) in THF (25 mL), cooled to 0° C., 1M LiAlH4 (880 μL, 797 mg, 0.880 mmol) was added, under N2, and the reaction solution was vortexed for 2 h. Upon addition, the reaction mixture changed from yellow to dark green in color. The reaction was quenched with potassium sodium tartrate sat. aq. sol. (25 mL), extracted with EtOAc (3×20 mL), washed with brine (1×40 mL), dried over MgSO4, and filtered. The crude material was purified by filtration through a plug of silica gel plug [eluting with EtOAc:CH2Cl2 1:1 (400 mL)] and concentrated, affording 366.3 mg (71%, 0.829 mmol) of the title compound, as a yellow solid; 1H NMR (CDCl3, 400 MHz) δ 4.82 (d, J=6.0 Hz, 2H), 5.15 (s, 2H), 7.05-7.11 (m, 1H), 7.32-7.43 (m, 7H), 7.44-7.49 (m, 2H), 7.52-7.61 (m, 2H), 7.73-7.78 (m, 1H), 7.87 (s, 1H), 8.05 (d, J=4.8 Hz, 1H); MS (ES+): m/z 441.9/443.9 (100/38) [MH+].

Provenance & Evidence