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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1410114Generated: October 28, 2026

Sodium Carbonate → HCID 68379404, compound

https://huagongshe.com/reaction/1410114

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantBenzene, 1-bromo-3-nitro-HCID 11457—
Reactant(2S)-2-methylpyrrolidineHCID 6999702—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 68379404HCID 6837940491%

Reaction Steps

A mixture of 1-bromo-3-nitrobenzene (1.43 g, 7.06 mmol), (S)-2-methylpyrrolidine (0.5 g, 5.88 mmol), Pd2(dba)3 (0.34 g, 0.59 mmol), X-Phos (0.56 g, 1.18 mmol) and sodium carbonate (1.77 g, 16.74 mmol) in the mixture of 1,4-dioxane (20 mL) and water (20 mL) was heated to reflux for 16 hours. Then water was added, extracted with ethyl acetate and organic layer washed brine dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1) to give (S)-2-methyl-1-(3-nitrophenyl)pyrrolidine (1.1 g, 91%) as red solid. LC-MS: 207 [M+H]+, tR=1.77 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08921383B2
Source datasetuspto-grants-2014_12
ORD IDord-1aa099bf04414baeb8e5121fa2a49a4c
Source noteuspto-grants-2014_12