Ethyl Acetate → HCID 178477568, compound

Participants

Reaction Steps

A solution of 5 g (13.4 mmol) of 4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenylamine in 150 mL of AcOH was treated with 2.5 g of Pt/C (10%) and hydrogenated for 72 hrs at atmospheric pressure under intense stirring. Filtration and evaporation of the solvent gave a yellow semisolid that was distributed between a 1M aqueous solution of NaOH and EtOAc. The combined organic phases were dried over Na2SO4 and evaporated to yield 4 g of crude product. Chromatography on silica gel with EtOAc and then EtOAc/MeOH 10:1 gave ca. 1.9 g (37%) of cis-4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexylamine and ca. 1.9 g (37%) trans-4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexylamine as a light yellow oil, MS: 380 (M+H)+.

Provenance & Evidence