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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 557826Generated: October 31, 2026

Toluene → Tert-butyl1-[4-(2-oxo-pyrrolidin-1-yl)phenyl]cyclopropanecarboxylate

https://huagongshe.com/reaction/557826

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium CarbonateHCID 11430—
Reactant1,2-Diaminocyclohexane, trans-HCID 43806—
ReactantTert-butyl 1-(4-bromophenyl)cyclopropanecarboxylateHCID 66661920—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventEthyl AcetateHCID 8857—
ProductTert-butyl1-[4-(2-oxo-pyrrolidin-1-yl)phenyl]cyclopropanecarboxylateHCID 66661882—

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of tert-butyl 1-(4-bromophenyl)cyclopropanecarboxylate (297.2 mg, 1.0 mmol), t-oxo-pyrrolidine (1.2 mmol), copper(I) iodide (20.0 mg, 0.1 mmol), (trans)-cyclohexane-1,2-diamine (22.8 mg, 0.2 mmol) and potassium carbonate (300.0 mg, 2.17 mmol) was dearated under vacuum and then charged with nitrogen. To the mixture was added toluene (2.0 mL). The resulting mixture was heated at 100° C. for overnight. Then ethyl acetate (10 mL) was added to the mixture. The resulting mixture was filtered through a pad of celite, and the solid was washed with additional ethyl acetate. The filtrate was concentrated. The residue was purified by flash chromatography with ethyl acetate/hexane to afford tert-butyl 1-[4-(2-oxo-pyrrolidin-1-yl)phenyl]cyclopropanecarboxylate.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08058288B2
Source datasetuspto-grants-2011_11
ORD IDord-f1209dbdabc143d8b809e92da26cf395
Source noteuspto-grants-2011_11