HCID 178444118, compound → Ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-6-n-butyl-4-oxo-1,4,5,6-tetrahydronicotinate

HRID 1464336Notes

Reaction equation

HRID 1464336 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][CH:22]=[C:23]([C:29](=[O:36])[CH:30]=[CH:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][N:21]2[CH:31]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:30][C:29](=[O:36])[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22]2)=[CH:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 178444118HCID 178444118, compound

Product 1

HCID 19087856Ethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-6-n-butyl-4-oxo-1,4,5,6-tetrahydronicotinateYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2-[(2'-t-butoxycarbonylbiphenyl-4-yl)methylaminomethylene]-3-oxo-4-nonenate (1.59 g, 3.23 mmol) in DMF (20 ml) and was heated under reflux for 4 hours. After cooling, the reaction solution was concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel. The column was eluted with ethyl acetate-hexane (7:3 to 8:2) to give 1.21 g (76.2%) of the title compound as an oil.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction solution was concentrated in vacuo
  4. customThe resulting residue was purified by column chromatography on silica gel
  5. washThe column was eluted with ethyl acetate-hexane (7:3 to 8:2)

Sources & evidence

ORD record
ord-88a98ffbc45c4faf8480b36b990fb154
Source dataset
uspto-grants-1994_04
Patent number
US05304565

Reaction notes

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