Ethyl 2-pyridylacetate → 2-Piperidineacetic acid, ethyl ester
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
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
- filtrationThe catalyst was filtered off
- customThe solvent was evaporated under reduced pressure, and ethanol
- additionwas added to the residue
- customthe solvent of the mixture was evaporated again under reduced pressure
- additionTo the residue, a small amount of water, diethyl ether (about 100 mL), and an excessive amount of potassium carbonate were added
- filtrationfollowed by filtration
- 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
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