TBAF tetrahydrofuran → 2-chloro-4-[(2S,3S)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]benzonitrile

HRID 1173674Notes

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)[CH2:12][C:11]2=[O:24])[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])[CH2:12][C:11]2=[O:24])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 595568912-chloro-4-[(4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-oxopyrrolidin-1-yl]benzonitrile

Product 1

HCID 595569692-chloro-4-[(2S,3S)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]benzonitrile

Procedure

Using 2-chloro-4-[(4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-oxopyrrolidin-1-yl]benzonitrile (1.2 g) and tetrabutylammonium fluoride-THF solution (4 mL, 1 mol/L), and in the same manner as in Example 15, the title compound was obtained as a colorless solid (yield: 690 mg, 62%).

Sources & evidence

ORD record: ord-b3a8648d91cd4f32bd2b7fd79ec29eda
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834051B2

Reaction notes

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