Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1445421Generated: October 31, 2026

Imidazole → 1-{[4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

https://huagongshe.com/reaction/1445421

Reaction equation

Participants

RoleNameHCIDCharge
ReactantImidazoleHCID 795—
Reactanttert-Butyldimethylsilyl chlorideHCID 28928—
Reactant1-[(4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-2-vinyl-cyclopropanecarboxylic acid ethyl esterHCID 66871268—
SolventDichloromethaneHCID 6344—
Product1-{[4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl esterHCID 6867566856%

Reaction Steps

Compound 123 (6.5 g) and imidazole (3.4 g, 50 mmol) was dissolved in DCM (100 ml), TBDMSCl (3.9 g, 26 mmol) was added and the reaction mixture was left stirring at room temperature overnight. The reaction mixture was washed with aqueous citric acid and brine, dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica (EtOAc/n-Heptane 50/50-100/0) to give the title compound (4.26 g, 56%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07666834B2
Source datasetuspto-grants-2010_02
ORD IDord-0a9b4f48876b4fc483fe907417eba76f
Source noteuspto-grants-2010_02