2,6-Difluoro-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile → Rac-2,6-difluoro-4-[(4r,5r)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile

HRID 1173664Notes

Reaction equation

HRID 1173664 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N:10]2[CH:14]([CH3:15])[C:13](=[O:16])[C:12]([CH3:18])([CH3:17])[C:11]2=[O:19])[CH:7]=[C:6]([F:20])[C:3]=1[C:4]#[N:5].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].C1COCC1>>[F:20][C:6]1[CH:7]=[C:8]([N:10]2[C@H:14]([CH3:15])[C@H:13]([OH:16])[C:12]([CH3:17])([CH3:18])[C:11]2=[O:19])[CH:9]=[C:2]([F:1])[C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 595569512,6-Difluoro-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrileHCID 131725857L-SELECTRIDE tetrahydrofuran

Product 1

HCID 67105494Rac-2,6-difluoro-4-[(4r,5r)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile

Procedure

Using 2,6-difluoro-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile (100 mg) and lithium tri(sec-butyl)borohydride-THF solution (0.539 mL, 1 mol/L), and in the same manner as in Example 5, the title compound was obtained as a colorless solid (yield: 67 mg, 67%).

Sources & evidence

ORD record
ord-a0e822e433d140cf97f1a9e3de147f0c
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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