Benzoyl chloride → HCID 178519538, compound

Participants

Reaction Steps

A solution of 50 mg (0.12 mmol) of trans cyclopropylmethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine in 3 mL of a 1:2-mixture of THF and 1,2-dichloroethane was treated with 0.03 mL (0.23 mmol) of NEt3 and 0.02 mL (0.14 mmol) of benzoylchloride. The mixture was stirred at RT for 2 hrs 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 redissolved in 2 mL of THF, treated with an excess of TBAF and distributed between a saturated aqueous solution of NH4Cl and Et2O. Drying of the combined organic phases over Na2SO4 and column chromatography on silica gel with heptane/EtOAc 2:1 gave 35 mg (72%) of trans N-cyclopropylmethyl-N-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-benzamide as a white solid, MS: 424, (M+H)+.

Provenance & Evidence