Dimethylformamide → Lenalidomide

HRID 332933

Reaktionsgleichung

Reaktionsgleichung von HRID 332933
[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-:3])=[O:2].CN(C)C=O>C(O)(C)C.C(O)C.CO>[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.[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-:3])=[O:2]

Komponenten

7

Edukt 2

HCID 6228DimethylformamideHCID 114717813-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

Produkt 2

HCID 216326LenalidomideHCID 114717813-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 887MethanolLösungsmittel2×HCID 3776IsopropanolLösungsmittel2×

Versuchsvorschrift

By catalytic hydrogenation of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione in solvents such as dimethylformamide, methanol, ethanol, isopropyl alcohol or mixture of these solvents at temperature 50-100.0° C. under pressure or bubbling of hydrogen gas at atmospheric pressure, then filteration of the catalyst followed by distillation under high vacuum Lenalidomide polymorphic form-I is obtained. The polymorphic form-I of Lenalidomide can also be obtained by transfer hydrogenation of 3-(4-nitro-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione using solvents dimethylformamide, methanol, ethanol, isopropyl alcohol or mixture of these solvents at temperature 50-100.0° C. using ammonium formate or formic acid as source of hydrogen. The precious metal catalysts used in the hydrogenation are Raney Nickel, palladium etc., followed by filteration of catalyst and distillation of the solvent under high vacuum.

Aufarbeitung

  1. custombubbling of hydrogen gas at atmospheric pressure
  2. distillationfilteration of the catalyst followed by distillation under high vacuum Lenalidomide polymorphic form-I
  3. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-3b1e366387a14741897b3bf6a17c7df5
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877932B2

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