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

HRID 226409
Notes
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Reaction equation

HRID 226409 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]3[N:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=3)[CH2:9]2)=[CH:4][CH:3]=1.[PH2](=O)O.N([O-])=O.[Na+].C([O-])(O)=O.[Na+]>O>[C:5]1([N:8]2[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]3[N:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=3)[CH2:9]2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 4124402Phosphinic AcidHCID 23668193Sodium NitriteHCID 86603717ethyl (2E)-3-(6-{[(3R)-1-(4-aminophenyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate

Product 1

HCID 86603716ethyl (2E)-3-(6-{[(3R)-1-phenyl-3-pyrrolidinyl]amino}-3-pyridinyl)acrylateYield 28.8%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

To a mixture of ethyl (2E)-3-(6-{[(3R)-1-(4-aminophenyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate (178 mg) and 50% phosphinic acid (5 mL) was added sodium nitrite (62.7 mg) in H2O at 4° C. The reaction mixture was stirred for 2 hours at 4° C. The resulting mixture was neutralized with saturated NaHCO3 and extracted with chloroform. The organic layer was dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(6-{[(3R)-1-phenyl-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate (49.0 mg).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-16cef425330043eb8f404228976ac7ea
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07557127B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes