2-Methoxy-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile → Rac-4-[(2r,3r)-3-hydroxy-2,3,4,4-tetramethyl-5-oxopyrrolidin-1-yl]-2-methoxybenzonitrile

HRID 1967332Notes

Reaction equation

HRID 1967332 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N:11]2[CH:15]([CH3:16])[C:14](=[O:17])[C:13]([CH3:19])([CH3:18])[C:12]2=[O:20])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[CH3:21][Mg]Br.C1COCC1>>[OH:17][C@:14]1([CH3:21])[C:13]([CH3:19])([CH3:18])[C:12](=[O:20])[N:11]([C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=2)[C@@H:15]1[CH3:16]

Participants

3

Reactant 2

HCID 595569862-Methoxy-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrileHCID 178420675HCID 178420675, compound

Product 1

HCID 67105765Rac-4-[(2r,3r)-3-hydroxy-2,3,4,4-tetramethyl-5-oxopyrrolidin-1-yl]-2-methoxybenzonitrile

Procedure

Using 2-methoxy-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile (100 mg) and methylmagnesium bromide-THF solution (3.67 mL, 1.0 mol/L), and in the same manner as in Example 2, the title compound was obtained as a colorless, solid (yield: 96 mg, 90%).

Sources & evidence

ORD record
ord-f537d9e320db4718adaa90ab77d6af46
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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