N,N-Diethylethanamine trihydrofluoride → HCID 118161760, compound

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A solution of 5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-3-iodo-1-isopropyl-1H-pyrazole (11.2 g, 19.7 mmol) and triethylamine trihydrofluoride (63 g, 391 mmol) in anhydrous tetrahydrofuran (100 mL) was heated at 70° C. for 6 h. Saturated aqueous sodium bicarbonate solution was added until the solution reached pH=7. The resulting aqueous mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (5:1 petroleum either/ethyl acetate) afforded crude 6-(3-iodo-1-isopropyl-1H-pyrazol-5-yl)bicyclo[3.1.0]hexan-3-ol as a pale yellow oil (6.6 g, 100%). LRMS: [M+H]+ 332.9.

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