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

HRID 712700

反応式

HRID 712700 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-499f8385f2b04d57bbd4bd6212d48e5e
出典データセット
uspto-grants-2015_11
特許番号
US09181272B2

関連ノート

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