Benzylamine → (+/-)-tert-Butyl 1-{[3-(benzylamino)-4-chlorophenyl](methoxy)methyl}cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

In a dry reaction flask which had been flushed with argon, 4.60 g (47.9 mmol) of sodium tert-butoxide were suspended in 100 ml of abs. toluene, and 5.2 ml (47.9 mmol) of benzylamine, 0.99 g (1.6 mmol) of rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1.83 g (2.0 mmol) of tris(dibenzylideneacetone)dipalladium and 15.0 g (39.9 mmol) of (+/−)-tert-butyl 1-[(3-bromo-4-chlorophenyl)(methoxy)methyl]cyclopropanecarboxylate were added. The reaction mixture was heated at 110° C. for 3 h. After cooling, ethyl acetate and saturated aqueous ammonium chloride solution were added and the mixture was filtered through Celite. The organic phase was washed with saturated ammonium chloride solution and saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1→20:1). This gave 12.0 g of the target compound (74.8% of theory).

Provenance & Evidence