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

HRID 712700

반응식

HRID 712700 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 1176674955-(5-Bromopyridin-3-YL)pyrrolidin-2-one수율 74.1%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-499f8385f2b04d57bbd4bd6212d48e5e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181272B2

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