Water → Methyl[2-(2-bromophenyl)ethyl]pentylcarbamate

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Reaction Steps

4.51 g of N-[2-(2-bromophenyl)ethyl]pentan-1-amine in suspension in 120 cm3 of anhydrous tetrahydrofuran are stirred under an inert atmosphere at 5° C. 2.33 cm3 of triethylamine, then 1.3 cm3 of methyl chloroformate are added to the reaction mixture. This mixture is then stirred for 20 h at a temperature close to 20° C. before being poured over a mixture of water and ice. The phases are stirred for 5 min, then separated. The aqueous phase is extracted 3 times with ethyl acetate. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated using a rotary evaporator under reduced pressure (5 kPa). The 6.33 g of oil obtained are purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 20% heptane/80% ethyl acetate). After concentrating the fractions under reduced pressure, 5.45 g of methyl[2-(2-bromophenyl)ethyl]pentylcarbamate are obtained in the form of a colorless oil

Provenance & Evidence