Acetonitrile → HCID 59447445, compound

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.

1. customTo a 100 ml round bottom flask equipped with a reflux condenser
2. customThe resulting reaction mixture
3. temperaturewas refluxed for 3 hours
4. customThe volatiles were removed
5. additionThe residue was diluted with 60 ml ethyl acetate and 50 ml saturated sodium carbonate
6. filtrationIt was filtered through a pad of celite
7. washThe organic portion from the filtrate was washed with 50 ml brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. dissolutionThe residue was redissolved in hexane/CH2Cl2 (9:1)
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-463490dc153745a1b3605db6ed01019d

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304434B2