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

HRID 1806716Notes

Reaction equation

[C:1]([O:5][C:6](=[O:14])[CH2:7]/[N:8]=[CH:9]/[CH2:10][CH:11]([CH3:13])[CH3:12])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:17]=[C:18](/[CH:22]=[C:23](/[C:26]2[CH:31]=[CH:30]C(Cl)=[CH:28][CH:27]=2)\[C:24]#[N:25])[CH:19]=[CH:20][CH:21]=1.C(N(CC)CC)C.Cl[CH2:41][Cl:42]>>[C:1]([O:5][C:6]([CH:7]1[CH:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[CH:17]=2)[C:23]([C:26]2[CH:27]=[CH:28][C:41]([Cl:42])=[CH:30][CH:31]=2)([C:24]#[N:25])[CH:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[NH:8]1)=[O:14])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 912043m-Chlorobenzylidene-p-chlorophenylacetonitrile

HCID 178446418HCID 178446418, compound

Product 1

HCID 67296830rac-(2R,3R,4R,5R)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-isobutyl-pyrrolidine-2-carboxylic acid tert-butyl esterYield 20%

Procedure

In a manner similar to the method described in Example 1c, [3-methyl-but-(E)-ylideneamino]-acetic acid tert-butyl ester prepared in Example 31a (2 g, 10 mmol) was reacted with (Z)-3-(3-chloro-phenyl)-2-(4-chloro-phenyl)-acrylonitrile (2 g, 7.3 mmol) prepared in Example 1b, AgF (1.3 g, 10 mmol), and triethylamine (2 g, 20 mmol) in dichloromethane (100 mL) at room temperature for 18 h to give rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-isobutyl-pyrrolidine-2-carboxylic acid tert-butyl ester as a white foam (0.7 g, 20%).

Sources & evidence

ORD record: ord-3dc07e40875d4fa882bf18e4a1d752e9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354444B2

Reaction notes

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