Carbon tetrabromide → Tert-butyl 3-[3-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate

Participants

Reaction Steps

6.0 g (13.29 mmol) of tert-butyl(+/−)-3-[3-({cyclopentyl[4-(hydroxymethyl)phenyl]acetyl}amino)-2-methylphenyl]propanoate were dissolved in 375 ml of dry THF, and 9.25 g (27.9 mmol) of carbon tetrabromide were added. Over a period of 1.5 h, 9.06 g (34.54 mmol) of triphenylphosphine were then added in small portions. The reaction mixture was stirred at RT for 5 h, and the solid was then filtered off and the filtrate was concentrated. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1). This gave 7.22 g (about 100% of theory, purity about 95%) of the title compound.

Provenance & Evidence