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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 70630Generated: October 26, 2026

Hydrogen Bromide → 6-{(E)-1-(4-Chlorophenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-cyclopropylpyridin-2(1H)-one

https://huagongshe.com/reaction/70630

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrogen BromideHCID 260—
Reactant1,4-DioxaneHCID 31275—
Reactant(5R)-5-[(E)-2-(4-chlorophenyl)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-oneHCID 67399304—
SolventWaterHCID 962—
Product6-{(E)-1-(4-Chlorophenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-cyclopropylpyridin-2(1H)-oneHCID 5845260468%

Reaction Conditions

Temperature65 °C

Reaction Steps

1,4-Dioxane (4 mL) and 48% hydrobromic acid (2 mL) were added to (5R)-5-[(E)-2-(4-chlorophenyl)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (250 mg), and the mixture was stirred at 65° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0→90:10) to give the title compound as a colorless powder (65 mg, 68% (two steps)).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822503B2
Source datasetuspto-grants-2014_09
ORD IDord-18ace6d546a04cda8fd5222d3300774f
Source noteuspto-grants-2014_09