4-(2,2-Difluoro-vinyl)-1-(4-methoxy-benzyl)-pyrrolidin-2-one → HCID 17948959, compound

HRID 2358227Notes

Reaction equation

HRID 2358227 reaction equation
[N+]([O-])([O-])=O.[NH4+].[Ce].[F:7][C:8]([F:25])=[CH:9][CH:10]1[CH2:14][N:13](CC2C=CC(OC)=CC=2)[C:12](=[O:24])[CH2:11]1>CC#N.O.O>[F:7][C:8]([F:25])=[CH:9][CH:10]1[CH2:14][NH:13][C:12](=[O:24])[CH2:11]1

Participants

5

Reactant 2

HCID 113001234-(2,2-Difluoro-vinyl)-1-(4-methoxy-benzyl)-pyrrolidin-2-oneHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 17948959HCID 17948959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
4 °C

Procedure

In a 200 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, cerium ammonium nitrate (11.2 g, 0.02 mol, 3 eq) is added to a solution of 4-(2,2-difluoro-vinyl)-1-(4-methoxy-benzyl)-pyrrolidin-2-one a4 (1.8 g, 6.8 mmol in MeCN/H2O (respectively 70 ml/110 ml) cooled at 4° C. After 5 h at 10° C., the reaction mixture is diluted with water, extracted with AcOEt, dried on MgSO4 and concentrated in vacuo. The residue is diluted with toluene, the solid is filtrated and the solvent is evaporated. The residue is purified by chromatography on silicagel (CH2Cl2/MeOH: 99/01 (v/v)) to afford fraction A1 (0.5 g of the expected compound) and fraction B (0.7 g of a mixture of synthetic intermediates and starting materials). Fraction B is again reacted with cerium ammonium nitrate as above (CAN: 0.78 g, MeCN (30 ml), H2O (50 ml)) to afford after purification, another fraction A2 (0.3 g). Fractions A1+A2 put together give 0.8 g of 4-(2,2-difluoro-vinyl)-pyrrolidin-2-one as (81%) contaminated by traces of 4-methoxybenzoic acid.

Workup

  1. extractionextracted with AcOEt
  2. customdried on MgSO4
  3. concentrationconcentrated in vacuo
  4. additionThe residue is diluted with toluene
  5. filtrationthe solid is filtrated
  6. customthe solvent is evaporated
  7. customThe residue is purified by chromatography on silicagel (CH2Cl2/MeOH: 99/01 (v/v))

Sources & evidence

ORD record
ord-1505e357d1324bbdacbdd5e05f2c14a1
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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