Potassium Fluoride → HCID 22615112, compound

Participants

Reaction Steps

To a cooled (0° C.) suspension of LiAlH4 (17 mg) in THF (1 ml) was added a solution of 3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-4-yloxy)-benzofuran-2-carboxylic acid ethyl ester (44 mg), the compound in Example 108, in THF (0.5 ml) and the resulting suspension was stirred at 0° C. for one hour. To the suspension was dropwise added a solution of KF (122 mg) in H2O (100 μl) at 0° C. over five minutes. The suspension was stirred at room temperature for 30 minutes and diluted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH=10:1 as a developing solvent) to give [3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-4-yloxy)-benzofuran-2-yl]-methanol (33 mg) as a colorless oil. FAB-MS: m/z 353 (MH+); 1H-NMR (CDCl3): δ 2.00 (4H, m), 2.38 (3H, s), 2.42 (2H, m), 2.68 (2H, m), 3.55 (2H, s), 4.51 (1H, m), 4.71 (2H, s), 6.59 (1H, d, J=8 Hz), 7.00 (1H, d, J=8 Hz), 7.13 (1H, t, J=8 Hz), 7.26 (1H, dd, J1=8 Hz, J2=5 Hz), 7.68 (1H, dt, J1=8 Hz, J2=2 Hz), 8.51 (1H, dd, J1=5 Hz, J2=2 Hz), 8.54 (1H, d, J=2 Hz).

Provenance & Evidence