Water → (S)-Methyl 2-(5-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403861Notes

Reaction equation

HRID 403861 reaction equation
[CH3:1][CH:2]([CH3:27])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5].[Cl-].[NH4+].C1COCC1.O>CCO.C(OCC)(=O)C.[Fe]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[C:9](=[O:26])[N:8]([C@@H:3]([CH:2]([CH3:27])[CH3:1])[C:4]([O:6][CH3:7])=[O:5])[CH2:16]3)=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 131731500(S)-Methyl 3-methyl-2-(5-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoate

Product 1

HCID 131731499(S)-Methyl 2-(5-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of example 222 (0.5 g, 0.00135 mol), iron (0.178 g, 0.00319 mol) and ammonium chloride (0.312 g, 0.00585 mol) are taken in EtOH:THF:H2O (7.5 mL; 5:2.5). The reaction mixture was refluxed for about 16 h. After completion of the reaction, the reaction mixture was filtered through celite. The filtrate was concentrated to obtain a solid residue, which was dissolved in ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The residue obtained was purified by column chromatography (silicagel, 30% ethyl acetate in petroleum ether) to obtain the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for about 16 h
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through celite
  4. concentrationThe filtrate was concentrated
  5. customto obtain a solid residue, which
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue obtained
  10. customwas purified by column chromatography (silicagel, 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-b2d1aab423fa4eefa5fc1656bab38680
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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