Ethyl bromoacetate → Ethyl 2-(3,3-bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetate

HRID 2408844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2408844
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH2:13][CH2:12][CH2:11][NH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>O1CCCC1>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12][CH2:11][N:10]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:9]2=[O:14])=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 673576463,3-Bis(4-fluorophenyl)piperidin-2-one

Produkt 1

HCID 67359841Ethyl 2-(3,3-bis(4-fluorophenyl)-2-oxopiperidin-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To the product from Example 23B (0.43 g, 1.50 mmol) as a solution in tetrahydrofuran (20 mL) was added potassium tert-butoxide (1.0 M in tetrahydrofuran) (1.80 mL, 1.80 mmol) via syringe under nitrogen followed by the addition of ethyl 2-bromoacetate (0.18 mL, 1.65 mmol). The reaction mixture heated at 80° C. and stirred overnight. The reaction mixture was cooled to room temperature, concentrated, diluted with ethyl acetate, washed with water and brine, dried with MgSO4, filtered and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (1:4) gave the title compound. MS (DCI) m/z 374 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washSilica gel chromatography eluting with ethyl acetate/hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-810a1770ebc24a62a746dbb976680e10
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815869B2

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