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

HRID 2052937Notes

Reaction equation

HRID 2052937 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][O:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][N:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C@@H:11]1[CH2:17][OH:18].[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:19])[CH2:4][O: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][OH:18]

Participants

5

Reactant 2

HCID 69020300[(Z)-4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-enyloxy]acetic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 69020934[4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-butoxy]-acetic acid methyl esterYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10 wt. %, 25 mg) was added to a solution of [(Z)-4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-enyloxy]-acetic acid methyl ester (318 mg, 1.17 mmol) in MeOH (5.0 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 2.25 h. The reaction mixture was filtered through celite, washing with MeOH, and the filtrate was concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (30% EtOAc/CH2Cl2→50% EtOAc/CH2Cl2, gradient, then 2% MeOH/CH2Cl2→5% MeOH/CH2Cl2) afforded 285 mg (89%) of [4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-butoxy]-acetic acid methyl ester.

Workup

  1. customby evacuating
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashing with MeOH
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification of the residue by flash column chromatography on silica gel (30% EtOAc/CH2Cl2→50% EtOAc/CH2Cl2, gradient

Sources & evidence

ORD record
ord-bb2bcd27b14b4462b1fd03e2954b0ae4
Source dataset
uspto-grants-2008_02
Patent number
US07326716B2

Reaction notes

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