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

HRID 1967342Notes

Reaction equation

HRID 1967342 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[CH:15]([CH3:16])[C:14](=[O:17])[C:13]([CH3:19])([CH3:18])[C:12]2=[O:20])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:21][Mg]Br.C1COCC1>>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C:12](=[O:20])[C:13]([CH3:19])([CH3:18])[C@:14]([OH:17])([CH3:21])[C@H:15]2[CH3:16])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 595569842-Chloro-3-methyl-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrileHCID 178420675HCID 178420675, compound

Product 1

HCID 67105643Rac-2-chloro-4-[(2r,3r)-3-hydroxy-2,3,4,4-tetramethyl-5-oxopyrrolidin-1-yl]-3-methylbenzonitrile

Procedure

Using 2-chloro-3-methyl-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile (40 mg) and methylmagnesium bromide-THF solution (1.38 mL, 1.0 mol/L), and in the same manner as in Example 2, the title compound was obtained as a colorless solid (yield: 24 mg, 57%).

Sources & evidence

ORD record
ord-17c356673fd24728a6ee03ce8bf5f19a
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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