Benzylamine → rac-Ethyl 2-[3-(benzylamino)-4-fluorophenyl]-trans-cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

Under argon, 361.5 m (3.8 mmol) of sodium tert-butoxide were suspended in 12.9 ml of toluene, and 900 mg (3.1 mmol) of (+/−)-trans-ethyl 2-(3-bromo-4-fluorophenyl)cyclopropanecarboxylate, 403 mg (3.8 mmol) of benzylamine, 28.7 mg (0.03 mmol) of tris(dibenzylideneacetone)dipalladium and 19.5 mg (0.03 mmol) of rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl were added successively. The mixture was heated at 110° C. for 4 h. The reaction mixture was then cooled to RT, 100 ml of ethyl acetate and 50 ml of saturated ammonium chloride solution were added and the mixture was filtered through celite. The organic phase was separated off, washed with in each case 50 ml of saturated ammonium chloride solution and saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The crude product was purified by preparative HPLC. This gave 262 mg of the target compound of a purity of 66% (18% of theory).

Provenance & Evidence