Trifluoroacetic acid → HCID 178479887, compound

Participants

Reaction Steps

Trifluoroacetic acid (2 mL) was added to a solution of (4S,7R)-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 (210 mg, 0.35 mmol) in dichloromethane (2 mL) and the resulting solution was stirred at room temperature for 3.5 h. Triethylsilane (56 μL, 0.35 mmol) was added and the solution was stirred for 5 min, and then evaporated and held under high vacuum overnight. The residue was taken up in dichloromethane and water and the pH was adjusted to ˜7 by adding saturated sodium bicarbonate solution. The layers were separated and the organic layer was dried (magnesium sulfate), filtered, evaporated, and chromatographed, eluting with 1-3% methanol/ethyl acetate to give (4S,7R)-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 (86 mg, 69%). ES(+)-MS (M+H) 355.

Provenance & Evidence