Ammonium formate → Lenalidomide

HRID 1525633Notes

Reaction equation

HRID 1525633 reaction equation
[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.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][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]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 114717813-(4-Nitro-1-oxo-1,3-dihydroisoindol-2-yl)piperidine-2,6-dione

Product 1

HCID 216326LenalidomideYield 89.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-(4-nitro-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-dioxopiperidine (7 g), 5% Pd/C (1.4 g) and ammonium formate (2.1 g) in methanol (35 ml) was stirred completely at room temperature for 2 hours. Pd/C was filtered and the filtrate concentrated to dry under reduced pressure. Recrystallization from heated isopropanol and washing with water gave 5.6 g of yellow crystal.

Workup

  1. filtrationPd/C was filtered
  2. concentrationthe filtrate concentrated
  3. customto dry under reduced pressure
  4. customRecrystallization
  5. temperaturefrom heated isopropanol
  6. washwashing with water

Sources & evidence

ORD record
ord-a80ce1909bfe48e48dde3d6d994e0694
Source dataset
uspto-grants-2015_07
Patent number
US09085530B2

Reaction notes

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