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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1365905Generated: November 1, 2026

Diisopropylethylamine → Rac-n-((3s,4r)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-isobutyramide

https://huagongshe.com/reaction/1365905

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant2-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 11267141—
Reactantrel-(3S,4R)-1-Benzyl-N-methyl-4-phenylpyrrolidin-3-amineHCID 59840122—
SolventDichloromethaneHCID 6344—
ProductRac-n-((3s,4r)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-isobutyramideHCID 8721193774%

Reaction Steps

A solution of 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride (the preparation of which is described in WO2002079134) (0.88 g, 2.76 mmol) in CH2Cl2 (2 ml) was added drop wise to a stirred solution of rac-((3S,4R)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-methyl-amine (0.72 g, 2.70 mmol) and ethyl-diisopropyl-amine (0.64 ml, 3.76 mmol) in CH2Cl2 (5 ml). The reaction mixture was stirred 1 h, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/H, 1:4) yielded 1.05 g (74%) of the title product as colorless foam.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07893062B2
Source datasetuspto-grants-2011_02
ORD IDord-2887b0bc2e884b99a5f1aa2cd5adfa71
Source noteuspto-grants-2011_02