Triethylamine → HCID 86653293, compound

Participants

Reaction Steps

To a solution of [(S)-3-(4-bromo-phenyl)-1-hydroxymethyl-propyl]-carbamic acid tert-butyl ester (11.5 g) and triethylamine (27.9 ml) in DMSO (70 ml) was added dropwise sulfur trioxide-pyridine complex (16.0 g) while the reaction mixture was cooled in a ice bath. The mixture was then stirred at room temperature for 30 min to afford a yellow solution. The reaction mixture was poured into EtOAc and extracted sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, heptane/EtOAc 3/1) to afford [(S)-3-(4-bromo-phenyl)-1-formyl-propyl]-carbamic acid tert-butyl ester as a yellow oil (7.3 g, 64%). MS (EI): 343 ([{81Br}M]+), 341 ([{79Br} M]+), 287 ([{81Br}M-C4H8]+), 285 ([{79Br} M-C4H8]+), 214 ([{81Br}M-C4H8—CO2]+), 212 ([{79Br} M-C4H8—CO2]+), 171, 169, 103, 57 ([C4H9]+).

Provenance & Evidence