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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1806759Generated: October 31, 2026

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

https://huagongshe.com/reaction/1806759

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactantm-Chlorobenzylidene-p-chlorophenylacetonitrileHCID 912043—
ReactantHCID 178451233HCID 178451233—
SolventDichloromethaneHCID 6344—
Productrac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-cyclohexyl-pyrrolidine-2-carboxylic acid tert-butyl esterHCID 6729705938%

Reaction Steps

In a manner similar to the method described in Example 1c, {[1-cyclohexyl-meth-(E)-ylidene]-amino}-acetic acid tert-butyl ester prepared in Example 50a (1.2 g, 5.3 mmol) was reacted with (Z)-3-(3-chloro-phenyl)-2-(4-chloro-phenyl)-acrylonitrile (1 g, 3.7 mmol) prepared in Example 1b, AgF (1.5 g, 12 mmol), and triethylamine (2 g, 20 mmol) in dichloromethane (100 mL) at room temperature for 20 h to give rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-cyclohexyl-pyrrolidine-2-carboxylic acid tert-butyl ester as a white foam (0.69 g, 38%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08354444B2
Source datasetuspto-grants-2013_01
ORD IDord-f6fe304d5a8148f096730cb7a58d605d
Source noteuspto-grants-2013_01