硼氢化钠 → 5-(5-Bromopyridin-3-YL)pyrrolidin-2-one

HRID 712700

反应方程式

HRID 712700 反应方程式
[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

参与物

5

反应物 3

HCID 4311764硼氢化钠HCID 6327182碲HCID 1176669483,3-Dibromo-5-(5-bromo-pyridin-3-yl)-pyrrolidin-2-one

产物 1

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

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

反应条件

温度
80 °C

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-499f8385f2b04d57bbd4bd6212d48e5e
来源数据集
uspto-grants-2015_11
专利号
US09181272B2

关联笔记

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