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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2046625Generated: October 26, 2026

Lithium Carbonate → 2-chloro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-3-methylbenzonitrile

https://huagongshe.com/reaction/2046625

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium CarbonateHCID 11125—
Reactant2-Chloro-4-fluoro-3-methylbenzonitrileHCID 44550971—
Reactant(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidineHCID 55299039—
SolventDimethyl SulfoxideHCID 679—
Product2-chloro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-3-methylbenzonitrileHCID 1594025416.3%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of compound 1 (1.56 g), 2-chloro-4-fluoro-3-methylbenzonitrile (1.27 g), lithium carbonate (1.16 g) and DMSO (37.5 ml) was stirred at 100° C. for 1 hr. The reaction mixture was cooled and partitioned between water and ethyl acetate. The organic layer was washed with water, dried (sodium sulfate), and concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane), and crystallized from ethyl acetate-hexane to give the title compound (357 mg) as crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08592452B2
Source datasetuspto-grants-2013_11
ORD IDord-03846190ece646a489999390347edb5b
Source noteuspto-grants-2013_11