Dichloromethane → 2-(2'-Fluorophenyl)-(4s,5s)-diphenyl-4,5-dihydroimidazole

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To a 100 ml flask was charged 5.00 g imidate 7 (19.6 mmol, 1 eq.), 4.16 g (S,S)-1, 2-diphenylethylenediamine (19.6 mmol, 1 eq.), 50 ml dichloromethane, and 6.3 ml triethylamine (45.3 mmol, 2.3 eq.) in the order given. After stirring 4 hours at ambient temperature, the reaction mixture was poured into 50 ml water, the phases separated, and the aq. phase reextracted with dichloromethane. The combined methylene chloride layers were washed with 2% aq. ammonium chloride, dried with magnesium sulfate, filtered, and the filtrate evaporated in vacuo to give an oil. This oil was dissolved in 25 ml boiling hexane, cooled to 0°, filtered and air dried to give 4.80 g of 2-(2′-fluorophenyl)-(4S,5S)-diphenyl4,5-dihydroimidazole 8 (78%) as a colorless solid. M.p. 122-124° C.; MS (ES+): MH+317; 19F NMR (CDCl3)δ: −113.6 ppm.

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