Sodium Hydroxide → ethyl (2E)-3-(6-{[(3R)-1-(4-aminophenyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate

HRID 226408Notes

Reaction equation

HRID 226408 reaction equation
C(OC([N:8]([C@@H:22]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=2)[CH2:23]1)[C:9]1[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)=O)(C)(C)C.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:33][C:30]1[CH:31]=[CH:32][C:27]([N:24]2[CH2:25][CH2:26][C@@H:22]([NH:8][C:9]3[N:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=3)[CH2:23]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 86603718ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(4-nitrophenyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate

Product 1

HCID 86603717ethyl (2E)-3-(6-{[(3R)-1-(4-aminophenyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylateYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(4-nitrophenyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate (297 mg) in ethanol (3 mL) was added tin(II) chloride (583 mg), and the mixture was heated at reflux for 6 hours. After cooling, the reaction mixture was basified with 2N sodium hydroxide and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(6-{[(3R)-1-(4-aminophenyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate (186 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0ed9e213ac9546179ccf83c9aa09ba66
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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