Triethylamine → Tert-butyl N-(3-oxo-1-phenylpropyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.63 g of tert-butyl 3-hydroxy-1-phenylpropylcarbamate (Formula 11) in 15 mL of dimethyl sulfoxide (DMSO) was added 2.72 mL of triethylamine. The solution was cooled to 0° C. and 3.1 g of sulfur trioxide pyridine complex in 15 mL of DMSO was added. The reaction mixture was stirred at room temperature for 1 hour then poured onto ice-water and extracted with ethyl acetate. The combined ethyl acetate layers were washed with 10% acetic acid, water, 5% sodium bicarbonate, and brine, dried over sodium sulfate and concentrated. Column chromatography (40% ethyl acetate/hexane) gave 1.2 g (74%) of tert-butyl-3-oxo-1-phenylpropylcarbamate (Formula 12) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.43 (s, 9H), 2.89-2.96 (m, 2H), 5.23 (br, 1H), 5.32 (br, 1H), 7.27-7.37 (m, 5H), 9.74 (m, 1H).

Provenance & Evidence