Trifluoroacetic acid → HCID 178479886, compound

Participants

Reaction Steps

Trifluoroacetic acid (4 mL) was added to a solution of (4R,7S)-1,7,8,8-tetramethyl-2-(3-trifluoromethyl-1-trityl-1H-pyrazol-4-ylmethyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (410 mg, 0.69 mmol) in dichloromethane (4 mL) and the yellow solution was stirred at room temperature for 4 h. Triethylsilane (110 μL, 0.69 mmol) was added and the solution was stirred at room temperature for 10 min. The solvent was evaporated using a rotary evaporator and the residue was held under high vacuum overnight. The residue was taken up in dichloromethane (50 mL), the solution was transferred to a separatory funnel and water (50 mL) was added. Aqueous saturated sodium hydrogen carbonate (1 Pasteur pipette) was added and the layers were separated. The organic layer was washed with brine (50 mL), dried (magnesium sulfate), filtered, evaporated, and purified using a Biotage 40S system, eluting with 1-3% methanol/ethyl acetate, to give (4R,7S)-1,7,8,8-tetramethyl-2-(3-trifluoromethyl-1H-pyrazol-4-ylmethyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (118 mg, 48%) as an off-white solid. APCI(+)-MS (M+H) 355.

Provenance & Evidence