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

HRID 1441379Notes

Reaction equation

HRID 1441379 reaction equation
[CH:1]1([NH:4][C:5]([C@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[O:6])[CH2:3][CH2:2]1.C([O-])=O.[NH4+]>CO.[Pd]>[CH:1]1([NH:4][C:5]([C@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68685984(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

Product 1

HCID 68689756(R)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamideYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide (Method 60; 142 g, 5.1 mmol) was dissolved in MeOH (50 ml), to this was added ammonium formate (1.6 g, 26 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 (1.20 g, 96%). Product rapidly turned black on exposure to air. The product was used immediately without any purification; m/z 246.

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-52aff16b10434bc88a358b970274a297
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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