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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1096937Generated: October 31, 2026

Pyrrolidine → Dimethyl 5-(pyrrolidin-1-yl)isophthalate

https://huagongshe.com/reaction/1096937

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyrrolidineHCID 31268—
ReactantPotassium Phosphate, TribasicHCID 62657—
Reactant2-(Di-tert-butylphosphino)biphenylHCID 2734215—
ReactantDimethyl 5-[[(Trifluoromethyl)sulfonyl]oxy]isophthalateHCID 10617248—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventEthyl AcetateHCID 8857—
ProductDimethyl 5-(pyrrolidin-1-yl)isophthalateHCID 57930958—

Reaction Conditions

Temperature80 °C

Reaction Steps

In a nitrogen atmosphere, a mixture of dimethyl 5-trifluoromethanesulfonyloxyisophthalate (1.37 g, 4.00 mmol), pyrrolidine (0.50 mL, 6.00 mmol), tris(dibenzylideneacetone)dipalladium(0) (37 mg, 0.040 mmol), 2-(di-tert-butylphosphino)biphenyl (24 mg, 0.080 mmol), potassium phosphate (1.19 g, 5.60 mmol) and 1,2-dimethoxyethane (12 mL) was stirred at 80° C. for 12 hours. After left cooled, the reaction mixture was diluted with ethyl acetate, filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography to obtain the title compound as a yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08138197B2
Source datasetuspto-grants-2012_03
ORD IDord-04d6cc786cb64d13b36840e67529af1e
Source noteuspto-grants-2012_03