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

HRID 1806755Notes

Reaction equation

[C:1]([O:5][C:6](=[O:13])[CH2:7]/[N:8]=[CH:9]/[CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:16]=[C:17](/[CH:21]=[C:22](/[C:25]2[CH:30]=[CH:29]C(Cl)=[CH:27][CH:26]=2)\[C:23]#[N:24])[CH:18]=[CH:19][CH:20]=1.C(N(CC)CC)C.Cl[CH2:40][Cl:41]>>[C:1]([O:5][C:6]([CH:7]1[CH:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[CH:16]=2)[C:22]([C:25]2[CH:26]=[CH:27][C:40]([Cl:41])=[CH:29][CH:30]=2)([C:23]#[N:24])[CH:9]([CH:10]([CH3:12])[CH3:11])[NH:8]1)=[O:13])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 912043m-Chlorobenzylidene-p-chlorophenylacetonitrile

HCID 178449146HCID 178449146, compound

Product 1

HCID 67296983rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-isopropyl-pyrrolidine-2-carboxylic acid tert-butyl esterYield 45%

Procedure

In a manner similar to the method described in Example 1c, [2-methyl-prop-(E)-ylideneamino]-acetic acid tert-butyl ester prepared in Example 49a (1 g, 5.4 mmol) was reacted with (Z)-3-(3-chloro-phenyl)-2-(4-chloro-phenyl)-acrylonitrile (0.85 g, 3.1 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-isopropyl-pyrrolidine-2-carboxylic acid tert-butyl ester as a white foam (0.64 g, 45%).

Sources & evidence

ORD record: ord-74a792d0ec79484bbcba2d76fc57b43b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354444B2

Reaction notes

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