Trifluoromethanesulfonic acid → HCID 178502735, Verbindung

HRID 1036535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036535
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH2:4][CH2:3]1.[CH2:14](OC(=N)C(Cl)(Cl)Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)S(O)(=O)=O>C1CCCCC1.C(Cl)Cl>[CH2:14]([O:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH2:4][CH2:3]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 178502733HCID 178502733, Verbindung

Produkt 1

HCID 178502735HCID 178502735, VerbindungAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21916607Dichloromethane cyclohexaneLösungsmittel

Versuchsvorschrift

To a mixture of cis-4-hydroxy-N-methoxy-N-methylcyclohexanecarboxamide (3.556 g, 0.0190 mol) and benzyl-2,2,2-trichloroacetimidate (4.0 mL, 0.021 mol, 1.1 eq) in cyclohexane/DCM (20 mL/10 mL) at 0° C. was added trifluoromethanesulfonic acid dropwise with stirring under nitrogen atmosphere over 30 min. There was an immediate precipitate. The mixture was stirred at room temperature for 15 h, filtered, and the filtrate washed with sodium bicarbonate solution and brine. The organic layer was concentrated and purified by silica gel column chromatography using petroleum ether/ethyl acetate (5/1) as eluent to give product as a colorless oil (5.079 g, 77%). 1H NMR (400 MHz, CDCl3) δ7.38-7.23 (m, 5H), 4.50 (s, 2H), 3.71 (s, 3H), 3.70-3.66 (m, 1H), 3.18 (s, 3H), 2.78-2.62 (m, 1H), 2.07-1.89 (m, 4H), 1.59-1.25 (m, 4H).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 15 h
  2. filtrationfiltered
  3. washthe filtrate washed with sodium bicarbonate solution and brine
  4. concentrationThe organic layer was concentrated
  5. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3693e2b52a184e8cbe0716ad0371d646
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546359B2

Notizen zur Reaktion

Wird geladen…