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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1362646Generated: October 30, 2026

Ethanol → (E)-1-[(1R,2S)-2-hydroxyindan-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one

https://huagongshe.com/reaction/1362646

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantWaterHCID 962—
ReactantSodium HydroxideHCID 14798—
Reactant(E)-5-[(1R,2S)-2-hydroxyindan-1-ylamino]-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]valeric acid ethyl esterHCID 66961755—
SolventEthyl AcetateHCID 8857—
Product(E)-1-[(1R,2S)-2-hydroxyindan-1-yl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-oneHCID 5917084572.8%

Reaction Steps

To an ethanol (2.0 mL) solution of (E)-5-[(1R,2S)-2-hydroxyindan-1-ylamino]-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]valeric acid ethyl ester (120 mg), 2N sodium hydroxide solution (1.0 mL) was added. After carrying out heat-refluxing of the reaction solution for 30 minutes and confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate=1:1->ethyl acetate->ethyl acetate:ethanol=10:1), and 78.9 mg of the title compound was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07880009B2
Source datasetuspto-grants-2011_02
ORD IDord-aede15d815644e31acaaaa547fdf03b3
Source noteuspto-grants-2011_02