Acetonitrile → HCID 59447445, compound

Participants

Reaction Steps

To a 100 ml round bottom flask equipped with a reflux condenser was added tert-butyl 3-(1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)azetidine-1-carboxylate (0.85 g, 2.09 mmol), ceric ammonium nitrate (1.37 g, 2.5 mmol) and 15 ml acetonitrile. The resulting reaction mixture was refluxed for 3 hours. The volatiles were removed. The residue was diluted with 60 ml ethyl acetate and 50 ml saturated sodium carbonate. It was filtered through a pad of celite. The organic portion from the filtrate was washed with 50 ml brine, dried over sodium sulfate, filtered and concentrated. The residue was redissolved in hexane/CH2Cl2 (9:1), filtered and concentrated to give 0.62 g yellow sticky solid. It is about 90% pure based on 1H NMR spectra. It was used for next step without further purification.

Provenance & Evidence