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

HRID 712700
Notes
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Reaction equation

HRID 712700 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-499f8385f2b04d57bbd4bd6212d48e5e
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181272B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes