Ammonium formate → (S)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide

HRID 1441371Notes

Reaction equation

HRID 1441371 reaction equation
[CH3:1][N:2]([CH3:19])[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][N:2]([CH3:19])[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 68687436(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide

Product 1

HCID 68686439(S)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid dimethylamideYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide (Method 52; 0.85 g) was dissolved in MeOH (50 ml), to this was added ammonium formate (1.0 g, 16 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 was removed in vacuo to yield the title compound as a brown gum (0.67 g, 87%). The 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. custom(reaction 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 was removed in vacuo

Sources & evidence

ORD record
ord-5cf5cd81d2234098b6d116d22a01a340
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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