2-Chloro-4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile → Rac-2-chloro-4-[(2r,3r)-2-ethyl-3-hydroxy-3,4,4-trimethyl-5-oxopyrrolidin-1-yl]benzonitrile

HRID 1967340Notes

Reaction equation

HRID 1967340 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[CH:14]([CH2:15][CH3:16])[C:13](=[O:17])[C:12]([CH3:19])([CH3:18])[C:11]2=[O:20])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:21][Mg]Br.C1COCC1>>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C:11](=[O:20])[C:12]([CH3:19])([CH3:18])[C@:13]([OH:17])([CH3:21])[C@H:14]2[CH2:15][CH3:16])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 595570162-Chloro-4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrileHCID 178420675HCID 178420675, compound

Product 1

HCID 67105654Rac-2-chloro-4-[(2r,3r)-2-ethyl-3-hydroxy-3,4,4-trimethyl-5-oxopyrrolidin-1-yl]benzonitrile

Procedure

Using 2-chloro-4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile (48 mg) and methylmagnesium bromide-THF solution (1.65 mL, 1.0 mol/L), and in the same manner as in Example 2, the title compound was obtained as a colorless solid (yield: 27 mg, 53%).

Sources & evidence

ORD record
ord-732f463821864809857820ccac08f2bc
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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