Triethylamine → 2,2,2-Trifluoro-1-(3-hydroxypiperidin-1-yl)ethanone

HRID 602127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602127
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C(N(CC)CC)C.[OH:17][CH:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1>C(O)C>[F:9][C:2]([F:1])([F:8])[C:3]([N:20]1[CH2:21][CH2:22][CH2:23][CH:18]([OH:17])[CH2:19]1)=[O:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 232933-Hydroxypiperidine

Produkt 1

HCID 589925842,2,2-Trifluoro-1-(3-hydroxypiperidin-1-yl)ethanoneAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl trifluoroacetate (1.31 mL, 11.0 mmol) and triethylamine (1.68 mL, 12.0 mmol) were added to 3-hydroxypiperidine (1.01 g, 10.0 mmol) in ethanol (10 mL). The mixture was stirred at room temperature for 8 hours. Subsequently, the reaction mixture was concentrated and water was added. The mixture was then extracted with ethyl acetate and the extract washed with brine and dried over magnesium sulfate. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 1.68 g (85%) of the desired compound as a colorless oil.

Aufarbeitung

  1. concentrationSubsequently, the reaction mixture was concentrated
  2. additionwater was added
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe extract washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1)

Quellen und Nachweise

ORD-Eintrag
ord-b402d2792c5e4687b940034055329816
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902367B2

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