Methyl 5-(ethyl{[4-(methyloxy)phenyl]methyl}amino)-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate → Methyl 5-(ethylamino)-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate

HRID 852652Notes

Reaction equation

HRID 852652 reaction equation
[CH2:1]([N:3](CC1C=CC(OC)=CC=1)[C:4]1[CH:5]=[C:6]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[C:7]([F:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])[CH3:2]>CCO.[Pd]>[CH2:1]([NH:3][C:4]1[CH:5]=[C:6]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[C:7]([F:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])[CH3:2]

Participants

4

Reactant 1

HCID 69357153Methyl 5-(ethyl{[4-(methyloxy)phenyl]methyl}amino)-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate

Product 1

HCID 69356192Methyl 5-(ethylamino)-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl 5-(ethyl{[4-(methyloxy)phenyl]methyl}amino)-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate (D155) (7 g, 17.5 mmol, 1 equiv) in EtOH (150 ml) was added 10% palladium on charcoal (50% wet, 1.4 g, 10% w/w) and the resulting mixture was stirred under an atmosphere of hydrogen (1 atm) for 3 h. The catalyst was filtered off through a pad of celite and the solution concentrated in vacuo. The residue was triturated with AcOEt/iso-hexane to give methyl 5-(ethylamino)-2-fluoro-3-(2-oxo-1-pyrrolidinyl)benzoate (B118) (4.8 g, 98%) as a pale greenish solid which was used in the next step without further purification. [M+H]+=281.2, RT=2.35 min.

Workup

  1. filtrationThe catalyst was filtered off through a pad of celite
  2. concentrationthe solution concentrated in vacuo
  3. customThe residue was triturated with AcOEt/iso-hexane

Sources & evidence

ORD record
ord-cee38b2e9dc24bedbf7e89fef4bcc186
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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