Hexane → 2-Amino-3'-tert-butoxycarbonylaminomethyl-5-(3-phenylpropyloxy)benzophenone

Participants

Reaction Conditions

Reaction Steps

N-Methyl-N-methyloxy-2-amino-5-(3-phenylpropyloxy)benzamide (1.0 g) and N-tert-butoxycarbonyl 3-bromobenzylamine (0.92 g) were dissolved in tetrahydrofuran (20 ml). The solution was cooled to −70° C., to which was added dropwise, while stirring, 12 ml of a hexane solution of n-butyl lithium (1.6 mol/L) over 20 minutes. To the mixture was then added water (50 ml) and ethyl acetate (50 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 2-amino-3′-tert-butoxycarbonylaminomethyl-5-(3-phenylpropyloxy)benzophenone as a yellow oily product (0.75 g).

Provenance & Evidence