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

HRID 226409Notes

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

Participants

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

extractionextracted with chloroform
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated in vacuo
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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