[(Z)-4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-enyloxy]-acetic acid ethyl ester → [4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-butoxy]-acetic acid ethyl ester

HRID 349346Notes

Reaction equation

HRID 349346 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][N:11]1[C:16](=[O:17])[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:18][OH:19])[CH3:2].[H][H]>[Pd].CCO>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:16](=[O:17])[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:18][OH:19])[CH3:2]

Participants

5

Reactant 2

HCID 69025613[(Z)-4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-enyloxy]-acetic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 69020752[4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-butoxy]-acetic acid ethyl esterYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10 wt. %, 15 mg) was added to a solution of [(Z)-4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-enyloxy]-acetic acid ethyl ester (290 mg, 1.02 mmol) in EtOH (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 3 h. The reaction mixture was filtered through celite, washing with EtOH, and the filtrate was concentrated in vacuo to afford 295 mg (quant. crude) of [4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-butoxy]-acetic acid ethyl ester.

Workup

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

Sources & evidence

ORD record
ord-890324a9c7b54bcda687ed32733cf3e3
Source dataset
uspto-grants-2007_02
Patent number
US07179820B2

Reaction notes

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