Diethyl Ether → HCID 178459293, compound

Participants

Reaction Steps

Compound 77c (670 mg, 1.65 mmol) obtained in Example 77 was dissolved in tetrahydrofuran (7 mL), to the solution was added methyl magnesium bromide (2.75 mL, a 3.0 mol/L solution in diethyl ether, 5.0 equivalents) under ice cooling, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride, and the mixture was warmed to room temperature and stirred for 10 minutes. The reaction mixture was extracted with chloroform, and the resulting organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:methanol=99:1). The product was converted into hydrochloride with a 4 mol/L solution of hydrogen chloride in dioxane, and then, after the solvent was evaporated, the product was recrystallized from ethyl acetate to obtain the title compound (460 mg, 68%).

Provenance & Evidence