2-(Trifluoromethyl)-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-(trifluoromethyl)benzonitrile

HRID 1967333Notes

Reaction equation

HRID 1967333 reaction equation
[F:1][C:2]([F:22])([F:21])[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].[CH3:23][Mg]Br.C1COCC1>>[OH:17][C@:14]1([CH3:23])[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]([C:2]([F:21])([F:1])[F:22])[CH:10]=2)[C@@H:15]1[CH3:16]

Participants

3

Reactant 2

HCID 595569412-(Trifluoromethyl)-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrileHCID 178420675HCID 178420675, compound

Product 1

HCID 67105617Rac-4-[(2r,3r)-3-hydroxy-2,3,4,4-tetramethyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

Procedure

Using 2-(trifluoromethyl)-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile (100 mg) and methylmagnesium bromide-THF solution (3.22 mL, 1.0 mol/L), and in the same manner as in Example 2, the title compound was obtained as a colorless solid (yield: 77 mg, 73%).

Sources & evidence

ORD record
ord-5749492b55d44d78b35bba319f6fc6db
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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