Diethyl Ether → HCID 178463683, compound

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Reaction Steps

A solution of 200 mg (0.43 mmol) of trans benzyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine (example 3.1) in 2 mL of pyridine was treated with 0.05 mL of acetic acid anhydride (0.51 mmol), stirred overnight at RT and distributed between a saturated aqueous solution of NH4Cl and Et2O. After drying of the combined organic phases over Na2SO4 and evaporation of the solvent, the residue was dissolved in 3.5 mL of THF and treated with 0.86 mL of a 1M BH3-solution in THF. The mixture was stirred at RT for 2 hrs, and the solvent evaporated. The residue was redissolved in THF treated with an excess of TBAF and solution was stirred for 2 hrs. Evaporation of the solvent and chromatography on silica gel with hexane/EtOAc 4:1 gave 64 mg (39%) of trans 2-[4-(benzyl-ethyl-amino)-cyclohexyl]-1,1,1,3,3,3-hexafluoro-propan-2-ol as a light yellow oil, MS: 384 (M+H)+.

Provenance & Evidence