(Z)-7-[2-Oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-enoic acid methyl ester → 7-[2-Oxo-6-(3-oxooctyl)-piperidin-1-yl]-heptanoic acid methyl ester

HRID 2052899Notes

Reaction equation

HRID 2052899 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][N:10]1[CH:15](/[CH:16]=[CH:17]/[C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][CH2:12][C:11]1=[O:25].[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:15]([CH2:16][CH2:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][CH2:12][C:11]1=[O:25]

Participants

5

Reactant 2

HCID 11726242(Z)-7-[2-Oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-enoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 100218997-[2-Oxo-6-(3-oxooctyl)-piperidin-1-yl]-heptanoic acid methyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10 wt. %, 5 mg) was added to a solution of (Z)-7-[2-oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-enoic acid methyl ester (40 mg, 0.11 mmol) in MeOH (3.0 mL). A hydrogen atmosphere was established by evacuating and refilling with hydrogen (3×) and the reaction mixture was stirred under a balloon of hydrogen for 19 h. The reaction mixture was filtered through celite, washing with MeOH, and the filtrate was concentrated in vacuo to afford 38 mg (94%) of the title compound.

Workup

  1. customby evacuating
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashing with MeOH
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-597297a9717b45c0b3fb6f3a091ea19b
Source dataset
uspto-grants-2008_02
Patent number
US07326716B2

Reaction notes

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