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

HRID 1173665Notes

Reaction equation

HRID 1173665 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].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].C1COCC1>>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@H:15]([CH3:16])[C@H:14]([OH:17])[C:13]([CH3:19])([CH3:18])[C:12]2=[O:20])[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 131725857L-SELECTRIDE tetrahydrofuran

Product 1

HCID 67105612Rac-2-chloro-4-[(4r,5r)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-3-methylbenzonitrile

Procedure

Using 2-chloro-3-methyl-4-(3,3,5-trimethyl-2,4-dioxopyrrolidin-1-yl)benzonitrile (23 mg) and lithium tri(sec-butyl)borohydride-THF solution (0.119 mL, 1 mol/L), and in the same manner as in Example 5, the title compound was obtained as a colorless solid (yield: 15 mg, 66%).

Sources & evidence

ORD record
ord-0172d24a827148ef8ee74e46a4fe24bd
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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