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

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl [(1S)-1-(4-bromophenyl)ethyl]carbamate (step 1, 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 compounds as white solids: 1H-NMR (CDCl3) δ 8.02–7.99 (2H, m), 7.37 (2H, d, J=8.4 Hz), 4.83 (2H, br.s), 3.91 (3H, s), 1.46–1.42 (12H, m).

Provenance & Evidence