Boron trifluoride etherate → HCID 66817075, compound

Participants

Reaction Steps

About 40 4AMS beads were added to a solution of (4-{2-[2-(4-isopropylidene-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3,5-dimethyl-phenyl)-methyl-carbamic acid tert-butyl ester (85.7 mg, 143 μmol) in dichloromethane (1.4 ml), and the mixture was stirred at room temperature for 10 minutes. Thereafter, BF3.Et2O (90.2 μl, 715 μmol) was added to the reaction mixture at 0° C., and the mixture was stirred at room temperature for three hours. The reaction mixture was quenched by adding triethylamine and diluted with ethyl acetate. The organic layer was then washed with a saturated aqueous sodium bicarbonate solution and water, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/0→92/8) to give 8-[2-(2,6-dimethyl-4-methylamino-phenyl)-ethanesulfonyl]-2-(4-isopropylidene-cyclohexyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (66.0 mg, 92%).

Provenance & Evidence