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

HRID 1441371
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1441371
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 68687436(R)-1-(4-Nitro-phenyl)-pyrrolidine-2-carboxylic acid dimethylamide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

(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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5cf5cd81d2234098b6d116d22a01a340
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07655652B2

Notizen zur Reaktion

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