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

HRID 1967338Notes

Reaction equation

HRID 1967338 reaction equation
[CH2:1]([CH:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([O:16][CH3:17])[CH:9]=2)[C:6](=[O:18])[C:5]([CH3:20])([CH3:19])[C:4]1=[O:21])[CH3:2].C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].C1COCC1>>[CH2:1]([C@H:3]1[N:7]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([O:16][CH3:17])[CH:9]=2)[C:6](=[O:18])[C:5]([CH3:20])([CH3:19])[C@H:4]1[OH:21])[CH3:2]

Participants

3

Reactant 2

HCID 595568974-(5-Ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)-2-methoxybenzonitrileHCID 131725857L-SELECTRIDE tetrahydrofuran

Product 1

HCID 67105799Rac-4-[(4r,5r)-5-ethyl-4-hydroxy-3,3-dimethyl-2-oxopyrrolidin-1-yl]-2-methoxybenzonitrile

Procedure

Using 4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)-2-methoxybenzonitrile (120 mg) and lithium tri(sec-butyl)borohydride-THF solution (0.629 mL, 1 mol/L), and in the same manner as in Example 5, the title compound was obtained as a colorless solid (yield: 93 mg, 77%).

Sources & evidence

ORD record
ord-23c2188a34ff4d0995fc5a142cd83fa8
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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