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Trifluoromethanesulfonic anhydride → 455954-80-0

HRID 1744679
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1744679
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O=[C:17]1[CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:20][N:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:18]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH2:18][N:19]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:20][CH2:21][C:22]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:5])=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 158529891-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate

Produkt 1

HCID 22228415455954-80-0Ausbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (12.4 mL, 73.7 mmol) was added over approximately 0.1 h, via syringe, to a stirred solution of the product of step B (27.1 g, 67.0 mmol) and N,N-diisopropylethylamine (14.0 mL, 80.4 mmol) in methylene chloride (250 mL) at −78° C. After allowing to warm to ambient temperature overnight, the reaction mixture was quenched with saturated aqueous sodium bicarbonate, poured into water and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient elution; 0–20% ethyl acetate/hexanes as eluent) afforded the title compound as an amber colored oil (17.6 g).

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. additionpoured into water
  3. extractionextracted three times with methylene chloride
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (gradient elution; 0–20% ethyl acetate/hexanes as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-39ec9578abbe4cd8b0bd37917c37e8f9
Quelldatensatz
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07015235B2

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