7-[(R)-2-((E)-3-Hydroxy-oct-1-enyl)-6-oxo-piperidin-1-yl]-heptanoic acid methyl ester → 7-[(R)-2-(3-Hydroxy-octyl)-6-oxo-piperidin-1-yl]-heptanoic acid methyl ester

HRID 2052920Notes

Reaction equation

HRID 2052920 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C@@H:11]1/[CH:17]=[CH:18]/[CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[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[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C@@H:11]1[CH2:17][CH2:18][CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 111994437-[(R)-2-((E)-3-Hydroxy-oct-1-enyl)-6-oxo-piperidin-1-yl]-heptanoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 114060367-[(R)-2-(3-Hydroxy-octyl)-6-oxo-piperidin-1-yl]-heptanoic acid methyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10 wt. %, 7 mg) was added to a solution of 7-[(R)-2-((E)-3-hydroxy-oct-1-enyl)-6-oxo-piperidin-1-yl]-heptanoic acid methyl ester (33 mg, 0.90 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 18.5 h. The reaction mixture was filtered through celite, washing with MeOH, and the filtrate was concentrated in vacuo to afford 28 mg (84%) 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-2244b12407a3423f948771edf4d4a264
Source dataset
uspto-grants-2008_02
Patent number
US07326716B2

Reaction notes

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