Diethyl Ether → 1,1-Dimethylethyl 4-(2,4-dichlorophenyl)hexahydro-1H-1,4-diazepine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of [1,4]diazepane-1-carboxylic acid tert-butyl ester (0.36 g, 1.77 mmol) in toluene (5 mL) was added tris(dibenzylideneacetone)-dipalladium(0) (0.040 g, 0.044 mmol), R(+)-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.027 g, 0.044 mmol), sodium t-butoxide (0.13 g, 1.33 mmol), and 1-bromo-2,4-dichlorobenzene (0.20 g, 0.89 mmol). The solution was heated to 100° C. for 2 h. The reaction was cooled to room temperature, diethylether (5 mL) was added and the resulting mixture filtered through a bed of diatomaceous earth. The residue was chromatographed on silica gel using hexane/ethyl acetate from 100% to 95% hexane in a gradient fashion, to give the title compound as a gum (0.13 g, 43%). The residue was used as is without further purification.

Provenance & Evidence