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

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

Participants

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

temperatureThe mixture is heated
temperatureThe mixture is cooled to room temperature
additionis added slowly
filtrationThe mixture is filtered through diatomaceous earth
washwashed with MeOH
concentrationThe filtrate is concentrated
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

Linked notes

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