Methyl iodide → HCID 57424240, compound

Participants

Reaction Steps

A solution of [4-(8,8-dimethyl-5-oxo-4-vinyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetic acid methyl ester (Intermediate 70, 0.205 g, 0.55 mmol) in dichloromethane (4 mL) and acetonitrile (2 mL) was treated with cyclopropyl amine (1 mL, 14.45 mmol). After 5 minutes, acetic acid (1 mL) was added followed by sodium cyanoborohydride (0.138 g, 2.2 mmol). The reaction mixture was stirred overnight at ambient temperature. It was then diluted with water and saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. The oil was dissolved in acetone (10 mL) and treated with potassium carbonate (0.227 g, 1.65 mmol) followed by methyl iodide (0.54 mL, 8.7 mmol) and the resulting reaction mixture was stirred overnight at ambient temperature. Diethyl ether was added to the reaction mixture and 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 4-5% ethyl acetate in hexane as the eluent afforded the title compound (0.14 g, 60%).

Provenance & Evidence