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
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
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