Tetrabutylammonium Fluoride → HCID 178464521, compound

Participants

Reaction Steps

A solution of 130 mg (0.23 mmol) of trans 1,2-dimethyl-1H-imidazole-4-sulfonic acid ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide in 2 mL of THF was treated with an excess of TBAF and stirred for 2 hrs at RT. Distribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases, evaporation of the solvent and column chromatography on silica gel with EtOAc/heptane 1:1 gave 42 mg (25%) of trans 1,2-dimethyl-1H-imidazole-4-sulfonic acid ethyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide as a yellow viscous oil, MS: 452 (M+H)+.

Provenance & Evidence