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

HRID 1967341Notes

Reaction equation

HRID 1967341 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[CH:15]([CH2:16][CH3:17])[C:14](=[O:18])[C:13]([CH3:20])([CH3:19])[C:12]2=[O:21])[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]([CH2:16][CH3:17])[C@H:14]([OH:18])[C:13]([CH3:20])([CH3:19])[C:12]2=[O:21])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 595568982-Chloro-4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)-3-methylbenzonitrileHCID 131725857L-SELECTRIDE tetrahydrofuran

Product 1

HCID 67105260Rac-2-chloro-4-[(4r,5r)-5-ethyl-4-hydroxy-3,3-dimethyl-2-oxopyrrolidin-1-yl]-3-methylbenzonitrile

Procedure

Using 2-chloro-4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)-3-methylbenzonitrile (310 mg) and lithium tri(sec-butyl)borohydride-THF solution (1.53 mL, 1 mol/L), and in the same manner as in Example 5, the title compound was obtained as a colorless solid (yield: 211 mg, 68%).

Sources & evidence

ORD record
ord-e6644725cae74e2fb16a16e94279780a
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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