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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1697600Generated: October 30, 2026

Lawesson's reagent → (2S,4R)-1-(2-Cyclohexyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

https://huagongshe.com/reaction/1697600

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLawesson's reagentHCID 87949—
ReactantCyclohexylhydrazine hydrochlorideHCID 207836—
Reactant(2S,4R)-1-(5-Methyl-2-phenyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid (1-cyano-cyclopropyl)-amideHCID 59543690—
Reactant(2R,4R)-1-(2-cyclohexyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 66770402—
Reactant(2R,4R)-1-(3-oxo-butyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 86646843—
Product(2S,4R)-1-(2-Cyclohexyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl EsterHCID 66770516—

Reaction Steps

In analogy to the procedure described in example 308d, a mixture of (2S,4R)-1-(3-oxo-butyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (example 192 f) and of (2R,4R)-1-(3-oxo-butyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with Lawesson's reagent (CAS Reg. No. 19172-47-5) and cyclohexylhydrazine hydrochloride (CAS Reg. No. 24214-73-1) to give a mixture of the title compound and (2R,4R)-1-(2-cyclohexyl-5-methyl-2H-pyrazol-3-yl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as brown oil. MS (ESI): m/z=500.3 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163793B2
Source datasetuspto-grants-2012_04
ORD IDord-04292a36a41848a7a9f8c89bcf6e2623
Source noteuspto-grants-2012_04