(Trifluoromethyl)trimethylsilane → HCID 59722702, compound

Participants

Reaction Steps

(Trifluoromethyl)trimethylsilane (0.273 mL, 1.85 mmol) and tetrabutylammonium fluoride (1.0 M in tetrahydrofuran; 74 μL, 0.074 mmol) were sequentially added to a solution of tert-butyl (6S,9R)-3-acetyl-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (150 mg, 0.37 mmol) in tetrahydrofuran (1 mL). After 5 min, additional (trifluoromethyl)trimethylsilane (100 μL, 0.678 mmol) and tetrabutylammonium fluoride (1.0 M in tetrahydrofuran; 25 μL, 0.025 mmol) were added. After 30 min, the reaction mixture was quenched with saturated sodium bicarbonate. The mixture was extracted with dichloromethane (3×), and the combined organic extracts were washed with water, saturated brine, dried over sodium sulfate, filtered and concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (55 mg). MS 476.2 (M+1).

Provenance & Evidence