Ethyl 2-pyridylacetate → 2-Piperidineacetic acid, ethyl ester

HRID 1437227Notes

Reaction equation

HRID 1437227 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:2].[H][H]>O.Cl.CO.[Pt](=O)=O>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)[CH3:2]

Participants

7

Procedure

Platinum(IV) oxide (15 mg) was added to a mixture of 2-(2-pyridyl)acetic acid ethyl ester (1.652 g) in water (1.25 mL) and concentrated hydrochloric acid (1.25 mL) in methanol (15 mL), and the resultant mixture was stirred in a hydrogen atmosphere at room temperature for 15 hours. The catalyst was filtered off. The solvent was evaporated under reduced pressure, and ethanol was added to the residue, and then the solvent of the mixture was evaporated again under reduced pressure. To the residue, a small amount of water, diethyl ether (about 100 mL), and an excessive amount of potassium carbonate were added, and the resultant mixture was stirred, followed by filtration. The solvent of the filtrate was evaporated under reduced pressure, to thereby give the title compound as an oily product (1.322 g, 77%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customThe solvent was evaporated under reduced pressure, and ethanol
  3. additionwas added to the residue
  4. customthe solvent of the mixture was evaporated again under reduced pressure
  5. additionTo the residue, a small amount of water, diethyl ether (about 100 mL), and an excessive amount of potassium carbonate were added
  6. filtrationfollowed by filtration
  7. customThe solvent of the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bb80192d81e645f196949e1edff32af7
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

Loading…