Acetyl chloride → HCID 178474532, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 50 mg (0.11 mmol) of trans benzyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine (example 3.1) in 1 mL of CH2Cl2 was treated with 0.1 mL of NEt3, cooled to 0° C. and treated with 0.14 mL (1.97 mmol) of acetylchloride. The mixture was stirred for 30 min and distributed between a saturated aqueous solution of NH4Cl and Et2O. The crude material obtained after drying of the combined organic phases over Na2SO4 and evaporation of the solvent was redissolved in 1 mL of THF, treated with an excess of TBAF and left to stir for 1 hr. Distribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4, evaporation of the solvent and chromatography on silica gel with EtOAc/heptane 1:1 gave 50 mg (95%) of trans N-benzyl-N-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-acetamide as a colorless viscous oil, MS: 398 (M+H)+.

Provenance & Evidence