tert-Butyl 4-(5-fluoro-6-nitro-1-oxoisoindolin-2-yl)piperidine-1-carboxylate → tert-Butyl 4-(6-amino-5-fluoro-1-oxoisoindolin-2-yl)piperidine-1-carboxylate

HRID 2093799Notes

Reaction equation

HRID 2093799 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[N:6]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[CH2:5]2>[Pd].CO>[NH2:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][N:6]([CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:17][CH2:16]3)[C:7]2=[O:14])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 67168225tert-Butyl 4-(5-fluoro-6-nitro-1-oxoisoindolin-2-yl)piperidine-1-carboxylate

Product 1

HCID 58257127tert-Butyl 4-(6-amino-5-fluoro-1-oxoisoindolin-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of tert-butyl 4-(5-fluoro-6-nitro-1-oxoisoindolin-2-yl)piperidine-1-carboxylate (Step 3, 240 mg, 0.72 mmol), Pd (10% wt on active carbon, 24 mg) and MeOH (20 mL) was evacuated to remove air, and then the reaction was stirred under a hydrogen balloon until the starting material is consumed. Pd/C was filtered off and the solution was concentrated in vacuo to afford tert-Butyl 4-(6-amino-5-fluoro-1-oxoisoindolin-2-yl)piperidine-1-carboxylate; ESMS m/z 350.2 (M+H+).

Workup

  1. customwas evacuated
  2. customto remove air
  3. customis consumed
  4. filtrationPd/C was filtered off
  5. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-e6e850a3211943f98708ff735de8c234
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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