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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 229860Generated: October 25, 2026

p-Toluenesulfonic acid → 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid methyl ester

https://huagongshe.com/reaction/229860

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acidHCID 6101—
Reactant(S)-(+)-TetrahydrofurfurylamineHCID 641530—
Reactant3-Oxo-2-[2-oxo-2-(2-trifluoromethoxy-phenyl)-ethyl]-butyric acid methyl esterHCID 69021229—
SolventMethanolHCID 887—
Product2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid methyl esterHCID 69023243—

Reaction Steps

To a solution of 250 mg of 3-oxo-2-[2-oxo-2-(2-trifluoromethoxy-phenyl)-ethyl]-butyric acid methyl ester in methanol was added 84 μl of (S)-tetrahydrofurfurylamine and 5 mg of p-toluene sulfonic acid. The reaction mixture was then heated at reflux for 24 hours. After such time the reaction mixture was allowed to cool to room temperature before being concentrated in vacuo and purified by column chromatography to give 171 mg of the title compound; MS (EI) 383.1 (M)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07563910B2
Source datasetuspto-grants-2009_07
ORD IDord-4a5cf6c4afb64be6b49837ecfc880f33
Source noteuspto-grants-2009_07