7-(2-Hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester → 7-(2-Hydroxymethyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl ester

HRID 349299Notes

Reaction equation

HRID 349299 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][N:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH:11]1[CH2:17][OH:18].[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:19])[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][CH:11]1[CH2:17][OH:18]

Participants

5

Reactant 2

HCID 690203407-(2-Hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 690230307-(2-Hydroxymethyl-6-oxo-piperidin-1-yl)-heptanoic acid methyl esterYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10 wt. %, 20 mg) was added to a solution of 7-(2-hydroxymethyl-6-oxo-piperidin-1-yl)-hept-5-ynoic acid methyl ester (180 mg, 0.67 mmol) in MeOH (6.0 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 23 h. The reaction mixture was filtered through celite, washing with MeOH, and the filtrate was concentrated in vacuo to afford 184 mg (quant.) of 7-(2-hydroxymethyl-6-oxo-piperidin-1-yl)-heptanoic 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

Sources & evidence

ORD record
ord-4748d340f699447a8860045892614cb8
Source dataset
uspto-grants-2007_02
Patent number
US07179820B2

Reaction notes

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