Hydrochloric Acid → HCID 71767641, compound

Participants

Reaction Steps

Methyl 3-ethyl-5-hydroxyisochroman-1-carboxylate (90 mg) was dissolved dichloromethane (1 mL) and 3,4-dihydro-2H-pyran (52 μL) and pyridinium p-toluenesulfonate (9.6 mg) were added. After 28 hours more 3,4-dihydro-2H-pyran (102 μL) and pyridinium p-toluenesulfonate (10 mg) were added and mixture was stirred for another 24 hours. 3,4-Dihydro-2H-pyran (200 μL) was then added and mixture was stirred overnight after which it was diluted with diethyl ether (5 ml) and washed with saturated NaHCO3-solution. Organic phase was dried with Na2SO4 and concentrated. Purification of the evaporation residue by column chromatography (ethyl acetate-heptane) afforded 37 mg of oil that was converted to 2-(3-ethyl-5-((tetrahydro-2H-pyran-2-yl)oxy)isochroman-1-yl)-4,5-dihydro-1H-imidazole (13 mg) using the synthesis method A3. The crude product of this procedure was dissolved in methanol (1 ml) and HCl solution in diethyl ether (2M, 39 μL) was added. After 2.5 hours reaction mixture was concentrated and the residue was taken in water (10 mL). The solution was washed with ethyl acetate and the water layer was concentrated in freeze dryer to afford the title compound. (Yield 6 mg).

Provenance & Evidence