Diazabicyclo[5.4.0]undec-7-ene → HCID 11253149, compound

HRID 2358235Notes

Reaction equation

HRID 2358235 reaction equation
Br[C:2]([F:17])([F:16])[CH2:3][CH:4]1[CH2:8][N:7]([CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[C:6](=[O:15])[CH2:5]1.N12CCCC=C1CCCCN2>C(Cl)(Cl)Cl>[F:17][C:2]([F:16])=[CH:3][CH:4]1[CH2:8][N:7]([CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[C:6](=[O:15])[CH2:5]1

Participants

4

Reactant 2

HCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 58911259HCID 58911259, compound

Product 1

HCID 11253149HCID 11253149, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a 50 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, 4-(2-bromo-2,2-difluoro-ethyl)-1-(1H-imidazol-1-ylmethyl)-pyrrolidin-2-one 17 (0.16 g, 0.52 mmol) and diazabicyclo [5.4.0]undec-7-ene (0.1 ml, 0.62 mmol) in CHCl3 (0.5 ml) are stirred overnight at room temperature. The reaction mixture is filtered, evaporated in vacuo, diluted with CH2Cl2 and the organic layer is washed with water, dried over MgSO4, filtered and evaporated in vacuo. The residue is purified by chromatography on silicagel (CH2Cl2/EtOH/NH4OH: 93.5/06/0.5 (v/v/v)) to afford 4-(2,2-difluorovinyl)-1-(1H-imidazol-1-ylmethyl)pyrrolidin-2-one 18 (0.092 g, 80%) which is crystallized as a maleic salt in THF.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated in vacuo
  3. additiondiluted with CH2Cl2
  4. washthe organic layer is washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue is purified by chromatography on silicagel (CH2Cl2/EtOH/NH4OH: 93.5/06/0.5 (v/v/v))

Sources & evidence

ORD record
ord-39de803e9a4f4ac9a9f45eced3e2ad43
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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