methyl 2-[(E)-2-phenylvinyl]isonicotinate → HCID 59291561, compound

HRID 383918Notes

Reaction equation

HRID 383918 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][N:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Pt]=O>[C:1]1([CH2:7][CH2:8][CH:9]2[CH2:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:16][CH2:17][NH:18]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 59291512methyl 2-[(E)-2-phenylvinyl]isonicotinate

Product 1

HCID 59291561HCID 59291561, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 2-[(E)-2-phenylvinyl]isonicotinate in acetic acid was added platinum oxide, followed by stirring at room temperature for 8 hours under a hydrogen atmosphere of 3 atm. The reaction mixture was filtered through Celite, and the filtrate was then concentrated under reduced pressure. To the residue were added an aqueous Na2CO3 solution, and the EtOAc was extracted. The organic layer was dried over MgSO4 and then concentrated under reduced pressure to obtain methyl 2-(2-phenylethyl)piperidine-4-carboxylate as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was then concentrated under reduced pressure
  3. additionTo the residue were added an aqueous Na2CO3 solution
  4. extractionthe EtOAc was extracted
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a25bff967b9c4f4b8cff8bd6d3a9ea6f
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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