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

HRID 879016
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 879016
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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 86679101N-[(1R)-Cyclohex-3-EN-1-YL]-2,2,2-trifluoro-acetamide

Produkt 1

HCID 866791002,2,2-trifluoro-N-[rel-(1R,3R,6S)-7-oxabicyclo[4.1.0]heptan-3-yl]acetamideAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-779238a88521453ba8e60ad09c5184df
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987498B2

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