Water → (RS)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide

HRID 1244550Notes

Reaction equation

HRID 1244550 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=O.O.[CH3:27][N:28](C)C=O>CN.C(O)C>[CH3:27][NH:28][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 68614055(RS)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

Product 1

HCID 9884445(RS)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6329MethylamineSolvent

Procedure

300 mg (0.87 mmol) (RS)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester is dissolved in a mixture of 1 ml N,N-dimethylformamide and 0.18 ml of a 33% solution of methylamine in ethanol. The reaction vessel is tightly stopped and hold at 120° C. for 48 hours. Water is added and the product extracted with ethyl acetate. Drying and evaporation yields 92 mg (31%) of a slightly yellowish product. MS: m/e=343.3 (M+H)+.

Workup

  1. extractionthe product extracted with ethyl acetate
  2. customDrying
  3. customevaporation
  4. customyields 92 mg (31%) of a slightly yellowish product

Sources & evidence

ORD record
ord-7ebc9fb2dd364de295d5365cc20dc5fe
Source dataset
uspto-grants-2006_10
Patent number
US07122562B2

Reaction notes

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