m-Chloroperbenzoic acid → 2,2,2-trifluoro-N-[rel-(1R,3R,6S)-7-oxabicyclo[4.1.0]heptan-3-yl]acetamide

Temperature

22.5 °C

9.2 g of mCPBA (70%) was charged to a vessel containing a cooled (10-15° C.) solution of 6 g of N-(cyclohex-3-en-1(R)-yl)-2,2,2-trifluoro-acetamide in 60 ml of chlorobenzene maintaining the temperature <30° C., and rinsed through with 3 ml of chlorobenzene. The mixture obtained was stirred at 20 to 25° C. for 1 h and the reaction was followed by TLC until completion. Upon completion of the reaction, the mixture obtained was heated to 38 to 42° C. for 2 h until reaction completion and cooled to 0 to −5° C., stirred for 30 min and the solid precipitate (mCBA) was filtered off and washed through with 2×3 ml of chlorobenzene. The resultant filtrate was washed with 30 ml of 10% sodium thiosulfate solution to remove peroxides, 2×30 ml of 5% NaHCO3 solution to ensure an pH of aqueous phase of >7, and 30 ml of H2O. The mixture obtained was concentrated to dryness. 5.08 g of 2,2,2-Trifluoro-N-(1R,3R,6S)-(7-oxa-bicyclo[4.1.0]hept-3-yl)-acetamide containing ca. 8% of anti (trans) epoxide in the form of a crystalline white solid was obtained.

1. additioncontaining
2. washrinsed through with 3 ml of chlorobenzene
3. customThe mixture obtained
4. customUpon completion of the reaction
5. customthe mixture obtained
6. temperaturewas heated to 38 to 42° C. for 2 h until reaction completion
7. temperaturecooled to 0 to −5° C.
8. stirringstirred for 30 min
9. filtrationthe solid precipitate (mCBA) was filtered off
10. washwashed through with 2×3 ml of chlorobenzene
11. washThe resultant filtrate was washed with 30 ml of 10% sodium thiosulfate solution
12. customto remove peroxides, 2×30 ml of 5% NaHCO3 solution
13. customThe mixture obtained
14. concentrationwas concentrated to dryness

ORD record

ord-779238a88521453ba8e60ad09c5184df

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987498B2