Benzyl 5-acetyl-4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyridine-3-carboxylate → 5-Acetyl4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyridine-3-carboxylic acid

HRID 420646Notes

Reaction equation

HRID 420646 reaction equation
[C:1]([C:4]1[CH:5]([C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=2)[CH:6]([C:22]([O:24]CC2C=CC=CC=2)=[O:23])[C:7](=[O:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2].[H][H]>[Pd].O1CCCC1>[C:1]([C:4]1[CH:5]([C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=2)[CH:6]([C:22]([OH:24])=[O:23])[C:7](=[O:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 59666193Benzyl 5-acetyl-4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyridine-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 596661955-Acetyl4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of benzyl 5-acetyl-4-(4-cyanophenyl)-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyridine-3-carboxylate (7.5 g, 14 mmol) (Example 6A) and 10%. palladium on charcoal (255 mg) in tetrahydrofuran (975 ml) is treated with hydrogen gas at room temperature under atmospheric pressure. After 15 minutes, the reaction is stopped and the solution is filtered and concentrated. The residue is immediately used in the next step without further purification and characterisation.

Workup

  1. filtrationthe solution is filtered
  2. concentrationconcentrated
  3. customThe residue is immediately used in the next step without further purification and characterisation

Sources & evidence

ORD record
ord-b2307c57007e45c0add8ada291b6c9b7
Source dataset
uspto-grants-2012_01
Patent number
US08097629B2

Reaction notes

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