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

HRID 1441379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441379
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

(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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-52aff16b10434bc88a358b970274a297
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655652B2

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