Tributylborane → HCID 9913119, compound

Participants

Reaction Conditions

Reaction Steps

A 7.3 ml portion of 1.54 M pentane solution of tert-butyl lithium was added dropwise to 100 ml of THF solution containing 2.48 g of trans-4-(4-cyano-3-trifluoromethylphenyl)-N-(6-methanesulfonyl-3-pyridyl)-2,5-dimethylpiperazine-1-carboxamide at −78° C., and then the mixture was stirred at −30° C. for 15 minutes. After cooling again to −78° C., this was mixed with 15.5 ml of 1.0 M tetrahydrofuran solution of tri-n-butyl borane, warmed up to room temperature spending 1 hour and then heated under refulx for 18 hours. Under ice-cooling, this was mixed with 5.91 g of sodium acetate, 50 ml of water and 491 mg of hydroxylamine-O-sulfonic acid and stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with saturated sodium bicarbonate solution and saturated brine in that order and dried over magnesium sulfate, and then the solvent was evaporated. The thus obtained mixture was subjected to a silica gel column chromatography and eluted with chloroform-methanol (9:1, v/v) to obtain 414 mg of the title compound. Thereafter, this was crystallized twice from ethanol to obtain 271 mg of the title compound as crystals.

Provenance & Evidence