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Water → 3-{2-[1-(6-Isobutyl-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dione

HRID 1663052
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1663052
Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]3[C:20](=[O:21])[CH2:19][O:18][C:17]3=[O:22])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.Br[Zn][CH2:25][CH:26]([CH3:28])[CH3:27].O.C(OCC)(=O)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:25]([C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]3[C:20](=[O:21])[CH2:19][O:18][C:17]3=[O:22])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1)[CH:26]([CH3:28])[CH3:27]
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Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 210969643-{2-[1-(6-Bromo-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dioneHCID 178448255HCID 178448255, Verbindung

Produkt 1

HCID 210969683-{2-[1-(6-Isobutyl-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2 g (5.43 mmol) of 3-{2-[1-(6-bromo-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dione, prepared in step 13.3, and 0.20 g (0.271 mmol) of dichlorobis(triphenylphosphine)palladium (Pd(PPh3)2Cl2) suspended in 10 ml of tetrahydrofuran are introduced under an inert atmosphere. 22 ml (10.80 mmol) of a solution (0.5 M) of bromo(isobutyl)zinc in tetrahydrofuran are then added. Stirring is continued at room temperature for 17 hours. The reaction mixture is poured into water and ethyl acetate. The phases are separated by settling, the aqueous phase is extracted twice with ethyl acetate, the combined organic phases are dried over sodium sulfate and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by chromatography on silica gel, eluting with a 20/80 mixture of ethyl acetate and cyclohexane.

Aufarbeitung

  1. additionare introduced under an inert atmosphere
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted twice with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by chromatography on silica gel
  8. washeluting with a 20/80 mixture of ethyl acetate and cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-b12c547a3d3846799374904fae6ade5e
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08034818B2

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