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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 390125Generated: October 29, 2026

Pyridine → 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/390125

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
Reactant4-Nitrobenzoyl chlorideHCID 8502—
Reactant2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 23571603—
SolventDichloromethaneHCID 6344—
Product2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 6687073872%

Reaction Conditions

Temperature0 °C

Reaction Steps

Compound 21a (11.8 g, 32.0 mmol) and pyridine (27 ml, 305 mmol) were dissolved in DCM (200 ml) and cooled to 0° C., 4-nitrobenzoyl chloride (6.6 g, 35.6 mmol) was added and the solution was stirred at room temperature overnight. The reaction mixture was washed with NaHCO3 (aq), aqueous citric acid and brine, dried over MgSO4 and evaporated on silica. The crude product was purified by column chromatography on silica (EtOAc/n-Heptane: 50:50) to give 11.84 g, 72% of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08383584B2
Source datasetuspto-grants-2013_02
ORD IDord-ecf25c2bbdc3430f96210f97feaea924
Source noteuspto-grants-2013_02