Bromomethylcyclopropane → HCID 178527322, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 500 mg (0.89 mmol) of trans N-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-benzenesulfonamide (example 1.3) in 10 mL of THF was cooled to −78° C. and treated dropwise with 0.72 mL of a 1.6 M BuLi solution in hexane. The solution was warmed to −40° C. within 30 min, treated with 0.43 mL (4.45 mmol) of bromomethylcyclopropane, allowed to reach RT and then refluxed overnight. An excess of TBAF was added and the mixture was stirred for an additional hour. Distribution of the crude mixture between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4, evaporation and chromatography on silica gel with CH2Cl2 gave 200 mg (49%) of trans N-cyclopropylmethyl-N-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-benzenesulfonamide, as a colorless viscous oil, MS: 460 (M+H)+.

Provenance & Evidence