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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1806739Generated: October 29, 2026

Triethylamine → rac-(2R,3R,4R,5S)-3,5-bis-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-pyrrolidine-2-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/1806739

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactantm-Chlorobenzylidene-p-chlorophenylacetonitrileHCID 912043—
ReactantHCID 178451237HCID 178451237—
SolventDichloromethaneHCID 6344—
Productrac-(2R,3R,4R,5S)-3,5-bis-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-pyrrolidine-2-carboxylic acid tert-butyl esterHCID 6729683844%

Reaction Steps

In a manner similar to the method described in Example 1c, {[1-(3-Chloro-phenyl)-meth-(E)-ylidene]-amino}-acetic acid tert-butyl ester prepared in Example 32a (2 g, 7.6 mmol) was reacted with (Z)-3-(3-chloro-phenyl)-2-(4-chloro-phenyl)-acrylonitrile (0.55 g, 2 mmol) prepared in Example 1b, AgF (1.3 g, 10 mmol), and triethylamine (1.9 g, 19 mmol) in dichloromethane (30 mL) at 50° C. for 20 h to give rac-(2R,3R,4R,5S)-3,5-bis-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-pyrrolidine-2-carboxylic acid tert-butyl ester as a white foam (0.45 g, 44%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08354444B2
Source datasetuspto-grants-2013_01
ORD IDord-81c24cc325384ed6959a493f3ae8532c
Source noteuspto-grants-2013_01