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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1675394Generated: October 31, 2026

1,1'-Carbonyldiimidazole → (1R,2S)-ethyl 1-(1H-imidazole-1-carboxamido)-2-vinylcyclopropanecarboxylate

https://huagongshe.com/reaction/1675394

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
Reactant(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate 4-methylbenzenesulfonateHCID 46737761—
SolventTetrahydrofuranHCID 8028—
Product(1R,2S)-ethyl 1-(1H-imidazole-1-carboxamido)-2-vinylcyclopropanecarboxylateHCID 5781668070%

Reaction Steps

Under nitrogen, (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate tosylate salt (5 g, 1 eq.) and CDI (2.7 g, 1.1 eq.) were dissolved in THF (50 mL) containing TEA (2.3 mL, 1.1 eq.). The reaction mixture was then refluxed overnight. The solvent was removed under reduced pressure. The residue was dissolved in DCM, and washed twice with water. The organic layer was dried over sodium sulfate and then concentrated. The residue was purified by chromatography on silica gel to yield compound 33 as pale yellow oil in 70% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08003659B2
Source datasetuspto-grants-2011_08
ORD IDord-829828b0f7654fb094befcc549e21ff9
Source noteuspto-grants-2011_08