3-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione → Lenalidomide

HRID 332934

Reaktionsgleichung

Reaktionsgleichung von HRID 332934
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13])([O-])=O.[H][H]>[Pd].CN(C=O)C>[CH:11]1[CH:10]=[C:9]2[C:8](=[O:13])[N:7]([CH:14]3[C:15](=[O:21])[NH:16][C:17](=[O:20])[CH2:18][CH2:19]3)[CH2:6][C:5]2=[C:4]([NH2:1])[CH:12]=1

Komponenten

5

Edukt 2

HCID 114717813-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dioneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 216326Lenalidomide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

Into a 5.0 L 4 necked RB flask, charged 100.0 g of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione, 10.0 g of 10% Pd/C and 3200 ml of DMF under nitrogen atmosphere. Stirred the mass and raise the reaction mass temperature to 60 -65° C. Started the hydrogen gas bubbling into reaction mass at temperature 60-65° C. for 6 hours. The progress of the reaction is monitored by TLC. Cooled the mass to temperature 25to 30° C. Filtered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere and wash with dimethylformamide; wet Pd/C is transferred into a polythene bag for recovery. Distilled off the above organic layer solvent completely under vacuum below 60° C. Charged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min. Filtered the solid and wash with 200 mL of ethyl acetate (Lot-II). Dried the above wet material in a oven at temperature 65-75° C. for 120-180 min. Dried Weight of the compound is 78.0 g.

Aufarbeitung

  1. temperatureraise the reaction mass temperature to 60 -65° C
  2. custombubbling into reaction mass at temperature 60-65° C. for 6 hours
  3. filtrationFiltered the catalyst Pd/C under plant vacuum in the presence of nitrogen atmosphere
  4. washwash with dimethylformamide
  5. distillationDistilled off the above organic layer solvent completely under vacuum below 60° C
  6. stirringCharged ethyl acetate 800 ml (lot-I) to the mass and stirred for 60 min
  7. filtrationFiltered the solid
  8. washwash with 200 mL of ethyl acetate (Lot-II)
  9. customDried the above wet material in a oven at temperature 65-75° C. for 120-180 min

Quellen und Nachweise

ORD-Eintrag
ord-3e1b7c87342243208b32e08ac9ebb8dc
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877932B2

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