HCID 58105211, compound → HCID 58105238, compound

HRID 1668528Notes

Reaction equation

HRID 1668528 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=1>C(O)C.[Pt](=O)=O>[OH:1][CH2:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 58105211HCID 58105211, compound

Product 1

HCID 58105238HCID 58105238, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

t-Butyl 3-(6-hydroxymethylpyridin-2-yl)-trans-acrylate (trans form) (16.86 g) was dissolved in 200 mL of ethanol, and 0.5 g of platinum dioxide was added to the solution, and then the mixture was stirred under atmospheric hydrogen pressure at room temperature for 5 hours. After that, the catalyst was filtrated off, another platinum dioxide (0.5 g) was added, and then the mixture was stirred under atmospheric hydrogen pressure at room temperature for 6 hours. The catalyst was filtrated off from the reaction mixture, and the solvent was removed under reduced pressure to give 16.13 g of t-butyl 3-(6-hydroxymethylpyridin-2-yl)propionate as a light yellow oil.

Workup

  1. filtrationAfter that, the catalyst was filtrated off
  2. additionanother platinum dioxide (0.5 g) was added
  3. stirringthe mixture was stirred under atmospheric hydrogen pressure at room temperature for 6 hours
  4. filtrationThe catalyst was filtrated off from the reaction mixture
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1f19d92c8be9406f9674afc07347c856
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

Loading…