Tetrabutylammonium Fluoride → (3R,4S)-4-(6-(tert-butyl)imidazo[1,2-a]pyridin-2-yl)-3-methylazetidin-2-one

HRID 1424203Notes

Reaction equation

HRID 1424203 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[C:12]([C@H:14]3[N:17]([Si](C(C)(C)C)(C)C)[C:16](=[O:25])[C@@H:15]3[CH3:26])[N:13]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[C:12]([C@H:14]3[NH:17][C:16](=[O:25])[C@@H:15]3[CH3:26])[N:13]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86699118HCID 86699118, compound

Product 1

HCID 86699117(3R,4S)-4-(6-(tert-butyl)imidazo[1,2-a]pyridin-2-yl)-3-methylazetidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(3R,4S)-4-(6-(tert-butyl)imidazo[1,2-a]pyridin-2-yl)-1-(tert-butyldimethylsilyl)-3-methylazetidin-2-one (Preparation 40) was dissolved in THF and 1 M tetrabutylammonium fluoride in THF (3 mL, 10 mmol) was added. The reaction mixture was stirred for 2 hours then the solvent was removed in vacuo. The intermediate was purified by silica gel column chromatography eluting with 0-100% CMA80 in dichloromethane to afford the title compound.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe intermediate was purified by silica gel column chromatography
  3. washeluting with 0-100%

Sources & evidence

ORD record
ord-49eedb815f404ac2a2f309eb496b9ad7
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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