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

HRID 1967346Notes

Reaction equation

[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([N:11]2[C@@H:15]([CH3:16])[C@@H:14]([O:17][Si](C(C)(C)C)(C)C)[CH2:13][C:12]2=[O:25])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.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])[CH2:13][C:12]2=[O:25])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 59556964HCID 59556964, compound

Product 1

HCID 595570242-chloro-4-[(4S,5S)-4-hydroxy-5-methyl-2-oxopyrrolidin-1-yl]-3-methylbenzonitrile

Procedure

Using 2-chloro-4-[(4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-oxopyrrolidin-1-yl]-3-methylbenzonitrile (500 mg) and tetrabutylammonium fluoride-THF solution (1.4 mL, 1 mol/L), and in the same manner as in Example 15, the title compound was obtained as a colorless solid (yield: 210 mg, 44%).

Sources & evidence

ORD record: ord-ce20f1ed20284c408b19115075815498
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420694B2

Reaction notes

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