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

HRID 345350Notes

Reaction equation

HRID 345350 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=1>C(O)(=O)C.[Pt]=O>[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4]1

Participants

4

Reactant 1

HCID 14541449Ethyl 4-(hydroxymethyl)picolinate

Product 1

HCID 19757810Ethyl 4-(hydroxymethyl)-piperidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 13.9 g of ethyl 4-(hydroxymethyl)-pyridine-2-carboxylate, 5 g platinum oxide in 250 ml acetic acid is hydrogenated at 50 lbs/in2Filtration, concentration in vacuo, and neutralization with potassium carbonate in methylene chloride yields an oil that is purified by flash chromatography using methylene chloride/methanol saturated with ammonia (20:1) to yield ethyl 4-(hydroxymethyl)-piperidine-2-carboxylate.

Workup

  1. concentrationis hydrogenated at 50 lbs/in2Filtration, concentration in vacuo, and neutralization with potassium carbonate in methylene chloride
  2. customyields an oil that
  3. customis purified by flash chromatography

Sources & evidence

ORD record
ord-e813e6eddbe546fd8caa68454d949046
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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