Methyl iodide → HCID 57424233, compound

Participants

Reaction Steps

A solution of 4,4-dimethyl-6-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydronaphthalene-1-one (U.S. Pat. No. 6,252,090, 0.85 g, 2.64 mmol) in dichloromethane (6 mL) and acetonitrile (3 mL) was treated with cyclopropyl amine (3 mL, 43.4 mmol). After 5 minutes, acetic acid (3 mL) was added followed by sodium cyanoborohydride (0.66 g, 10.55 mmol). The reaction was stirred overnight at ambient temperature. It was then diluted with water and saturated aqueous sodium carbonate solution and extracted with ethyl acetate. The combined organic extract was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. The oil was dissolved in acetone (20 mL) and treated with potassium carbonate (1.08 g, 7.8 mmol) and methyl iodide (1.6 mL, 26 mmol). The resulting reaction mixture was stirred at ambient temperature overnight. The solids were filtered off, the filtrate was evaporated in vacuo and the residue was subjected to flash column chromatography over silica gel (230–400 mesh) to afford the title compound (0.85 g, 87%) as a colorless oil.

Provenance & Evidence