TBAF tetrahydrofuran → Rac-2-chloro-4-[(4r,5r)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile

HRID 1967344Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C@H:14]([CH3:15])[C@H:13]([O:16][Si](C(C)(C)C)(C)C)[C:12]([CH3:25])([CH3:24])[C:11]2=[O:26])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C@H:14]([CH3:15])[C@H:13]([OH:16])[C:12]([CH3:25])([CH3:24])[C:11]2=[O:26])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 67105796Rac-2-chloro-4-[(4r,5r)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile

Product 1

HCID 67105434Rac-2-chloro-4-[(4r,5r)-4-hydroxy-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile

Procedure

Using rac-2-chloro-4-[(4R,5R)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]benzonitrile (400 mg) and tetrabutylammonium fluoride-THF solution (3 mL, 1 mol/L), and in the same manner as in Example 15, the title compound was obtained as a colorless solid (yield: 204 mg, 72%).

Sources & evidence

ORD record: ord-297917c846c54f9791b39e2801828415
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420694B2

Reaction notes

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