Ammonium formate → (R)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid methylamide

HRID 1441375Notes

Reaction equation

HRID 1441375 reaction equation
[CH3:1][NH:2][C:3]([C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)=[O:4].C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][NH:2][C:3]([C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1)=[O:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68688348(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid methylamide

Product 1

HCID 68685541(R)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid methylamideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid methylamide (Method 56; 1.2 g, 4.8 mmol) was dissolved in MeOH (50 ml), to this was added ammonium formate (1.5 g, 24 mmol) and palladium (0.1 g). The reaction was heated at reflux for 60 minutes; reaction decolourised. MeOH was removed in vacuo and saturated ammonium chloride (50 ml) was added, the system was extracted with DCM (2×100 ml), dried and solvent removed in vacuo to yield the title compound as a brown gum (1.0 g, 95%). Product rapidly turned black on exposure to air. The product was used immediately without any purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 60 minutes
  3. customreaction decolourised
  4. customMeOH was removed in vacuo and saturated ammonium chloride (50 ml)
  5. additionwas added
  6. extractionthe system was extracted with DCM (2×100 ml)
  7. customdried
  8. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-28ecf030050147ee83a79527065d8cc7
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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