tert-Butanol → Methyl 2-(4-bromophenyl)-1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of diphenyl phosphorazidate (7.59 g), 2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropanecarboxylic acid (7.5 g), triethylamine (3.84 mL) in a mixture of toluene (300 mL) and tert-butanol (300 mL) was heated at 85° C. for 10 h. The mixture was diluted with water and the mixture was extracted with ether, washed with 5% aqueous citric acid, followed by saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. The crude product was purified by flash silica chromatography, eluting with 1:1 diethyl ether/isohexane. Pure fractions were evaporated to dryness to afford methyl 2-(4-bromophenyl)-1-(tert-butoxycarbonylamino)cyclo-propanecarboxylate (4.60 g) as a colourless solid.

Provenance & Evidence