Sodium borohydride → 5-(5-Bromopyridin-3-YL)pyrrolidin-2-one

HRID 712700

Reaktionsgleichung

Reaktionsgleichung von HRID 712700
[BH4-].[Na+].[Te].Br[C:5]1(Br)[CH2:9][CH:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([Br:16])[CH:15]=2)[NH:7][C:6]1=[O:17]>C(O)C>[Br:16][C:14]1[CH:15]=[C:10]([CH:8]2[NH:7][C:6](=[O:17])[CH2:5][CH2:9]2)[CH:11]=[N:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 6327182TelluriumHCID 1176669483,3-Dibromo-5-(5-bromo-pyridin-3-yl)-pyrrolidin-2-one

Produkt 1

HCID 1176674955-(5-Bromopyridin-3-YL)pyrrolidin-2-oneAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Sodium borohydride (0.74 g, 19.6 mmol) is suspended in ethanol (17 mL) and tellurium metal powder (1.25 g, 9.78 mmol) is added in portions. The mixture is heated under reflux (external temperature 80° C.) for 15 min and the mixture becomes a light purple color. The mixture is cooled to room temperature. 3,3-Dibromo-5-(5-bromo-pyridin-3-yl)-pyrrolidin-2-one (0.65 g, 1.63 mmol) dissolved in EOH (5 mL) is added slowly. The mixture is stirred at room temperature over the weekend (72 h). The mixture is filtered through diatomaceous earth and washed with MeOH. The filtrate is concentrated. The resulting crude product is purified by normal phase chromatography using 0-6% MeOH in DCM as the gradient to afford 5-(5-bromo-pyridin-3-yl)-pyrrolidin-2-one (291 mg, 74% yield).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureThe mixture is cooled to room temperature
  3. additionis added slowly
  4. filtrationThe mixture is filtered through diatomaceous earth
  5. washwashed with MeOH
  6. concentrationThe filtrate is concentrated
  7. customThe resulting crude product is purified by normal phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-499f8385f2b04d57bbd4bd6212d48e5e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181272B2

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