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

HRID 1848390Notes

Reaction equation

HRID 1848390 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]>CO.[Pt](=O)=O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 1

HCID 75960Ethyl 2-pyridylacetate

Product 1

HCID 4369812-Piperidineacetic acid, ethyl esterYield 97.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

At rt a mixture of ethyl 2-(pyridin-2-yl)acetate (3.0 g, 18 mmol) and platinum (IV) oxide (0.825 g, 3.63 mmol) in methanol (25 mL) was subject to hydrogenation at 50 psi for 18 h. After filtration, the filtrate was concentrated to afford Intermediate 22A (3.0 g, 96%) as a clear oil. HPLC/MS (Method L) RT=0.99 min, [M+1]+ 172.2.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d2e1f82097664fae8be84d083431907b
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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