Ethyl 4-(2-hydroxyethyl)picolinate → Ethyl 4-(2-hydroxyethyl)piperidine-2-carboxylate

HRID 345343Notes

Reaction equation

HRID 345343 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=1>C(O)(=O)C.[Pt]=O>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][NH:7][CH:6]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:5]1

Participants

4

Reactant 1

HCID 19757799Ethyl 4-(2-hydroxyethyl)picolinate

Product 1

HCID 19757829Ethyl 4-(2-hydroxyethyl)piperidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 8.37 g of ethyl 4-(2-hydroxyethyl)-pyridine-2-carboxylate in 130 ml acetic acid and 4 g platinum oxide is hydrogenated at 50 lbs/in2. Filtration, concentration in vacuo, neutralization with potassium carbonate and extraction with methylene chloride yields an oil that is purified by flash chromatography using methylene chloride/methanol saturated with ammonia (20:1) to yield ethyl 4-(2-hydroxyethyl)-piperidine-2-carboxylate.

Workup

  1. filtrationFiltration, concentration in vacuo, neutralization
  2. extractionwith potassium carbonate and extraction with methylene chloride
  3. customyields an oil that
  4. customis purified by flash chromatography

Sources & evidence

ORD record
ord-71d3cb5cf1974ae6a157575efc5397e0
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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