Diethyl Ether → (S)-Methyl 4-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of tert-butyl [(1S)-1-(4-bromophenyl)ethyl]carbamate (step 3, 14.73 g, 49.1 mmol), 1,3-bis(diphenylphosphino)-propane (2.03 g, 4.91 mmol), palladium (II) acetate (1.10 g, 4.91 mmol), triethylamine (20.5 mL, 147 mmol), N,N-dimethylforamide (120 mL) and methanol (180 mL) was stirred at 80° C. for 16 h under carbon monoxide atmosphere. After cooling to room temperature, the mixture was diluted with ether (800 mL) and washed with water (500 mL×3). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (5:1) to afford 12.83 g (94%) of the title compound as white solids:

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