m-Chloroperbenzoic acid → 2,2,2-trifluoro-N-[rel-(1R,3R,6S)-7-oxabicyclo[4.1.0]heptan-3-yl]acetamide
反応式
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C@@H:12]1([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]1>ClC1C=CC=CC=1>[F:21][C:20]([F:22])([F:23])[C:19]([NH:18][C@@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:14]([O:9]2)[CH2:13]1)=[O:24]参加物
4
反応条件
- 温度
- 22.5 °C
実験手順
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.