Methyl iodide → HCID 69075764, compound

Participants

Reaction Steps

A solution of {4-[8,8-dimethyl-5-oxo-4-(2-trimethylsilanyl-ethoxymethoxy)-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-acetic acid methyl ester (Intermediate 74, 0.905 g, 1.84 mmol) in dichloromethane (8 mL) and acetonitrile (4 mL) was treated with cyclopropyl amine (4 mL, 57.8 mmol). After 5 minutes, acetic acid (4 mL) was added followed by sodium cyanoborohydride (0.46 g, 7.32 mmol). The reaction mixture was stirred overnight at ambient temperature. It was then diluted with water and saturated aqueous sodium carbonate solution and extracted with dichloromethane (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. The oil was dissolved in acetone (15 mL) and treated with potassium carbonate (0.745 g, 5.4 mmol) followed by methyl iodide (1.2 mL, 19 mmol) and the resulting reaction mixture was stirred overnight at ambient temperature. The precipitated solids were filtered off, the filtrate was evaporated in vacuo to a residue. Flash column chromatography over silica gel (230-400 mesh) using 2-20% ethyl acetate in hexane as the eluent afforded the title compound (0.6 g, 63%).

Provenance & Evidence