Tetrabutylammonium Fluoride → HCID 91506330, compound

Participants

Reaction Steps

To a solution of 30 mg of rac-isobutyric acid (1R*,2R*,4R*)-2-[2-({3-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propyl}-methyl-amino)-ethyl]-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester in 0.5 mL of anh. THF was added dropwise 0.2 mL of a 1M solution of TBAF in THF. The reaction mixture was refluxed for 6 h, diluted with DCM and washed with sat.-NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using EtOAc/MeOH/NEt3 from 100/0/1 to 90/10/1 as eluant to yield 14 mg of rac-isobutyric acid (1R*,2R*,4R*)-2-(2-{[3-(4,5-diphenyl-1H-imidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester as a yellowish solid.

Provenance & Evidence