HCID 22241213, compound → 3-(4-Amino-1,3-dioxoisoindolin-2-yl)-3-fluoro-2,6-dioxo-5-acetoxypiperidine

HRID 892000Notes

Reaction equation

HRID 892000 reaction equation
[F:1][C:2]1([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[N+:24]([O-])=O)[C:15]2=[O:27])[CH2:7][CH:6]([O:8][C:9](=[O:11])[CH3:10])[C:5](=[O:12])[NH:4][C:3]1=[O:13]>CO.[Pd]>[NH2:24][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:21]=1[C:22](=[O:23])[N:14]([C:2]1([F:1])[CH2:7][CH:6]([O:8][C:9](=[O:11])[CH3:10])[C:5](=[O:12])[NH:4][C:3]1=[O:13])[C:15]2=[O:27]

Participants

4

Reactant 1

HCID 22241213HCID 22241213, compound

Product 1

HCID 222412033-(4-Amino-1,3-dioxoisoindolin-2-yl)-3-fluoro-2,6-dioxo-5-acetoxypiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-fluoro-3-(4-nitro-1,3-dioxoisoindolin-2-yl)-2,6-dioxo-5-acetoxypiperidine (1.0 g, 2.6 mmol) and Pd/C (10%, 0.1 g) in methanol (100 mL) is shaken under hydrogen (50–60 psi) for 3 hours. The suspension is filtered through a pad of Celite and washed with methanol to give 3-(4-amino-1,3-dioxoisoindolin-2-yl)-3-fluoro-2,6-dioxo-5-acetoxypiperidine which is further purified by column chromatography.

Workup

  1. filtrationThe suspension is filtered through a pad of Celite
  2. washwashed with methanol

Sources & evidence

ORD record
ord-af4d692e571f434b9b815b51e60b0084
Source dataset
uspto-grants-2006_02
Patent number
US07005438B2

Reaction notes

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