HCID 19084743, compound → HCID 19084778, compound

HRID 962414Notes

Reaction equation

HRID 962414 reaction equation
[I-].[CH3:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([C:16]([OH:18])=[O:17])([OH:15])[P:11]([OH:14])([OH:13])=[O:12]>[Pd].O>[OH:15][C:10]([P:11]([OH:13])([OH:14])=[O:12])([CH2:9][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][N:3]1[CH3:2])[C:16]([OH:18])=[O:17]

Participants

4

Reactant 1

HCID 19084743HCID 19084743, compound

Product 1

HCID 19084778HCID 19084778, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 1 g of 1-methyl-2-(2-carboxy-2-hydroxy-2-phosphonoethyl)pyridinium iodide and 0.5 g of palladium on charcoal catalyst in 50 ml of distilled water is hydrogenated on a Parr apparatus at 40 PSI for about 2 days. The catalyst is removed by filtration, and the filtrate is evaporated to dryness. The residue is triturated with ethanol to give a solid which is collected by filtration. It is recrystallized from water/ethanol to afford 2-hydroxy-3-(1-methyl-2-piperidinyl)-2-phosphonopropanoic acid.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate is evaporated to dryness
  3. customThe residue is triturated with ethanol
  4. customto give a solid which
  5. filtrationis collected by filtration
  6. customIt is recrystallized from water/ethanol

Sources & evidence

ORD record
ord-50648f6d39d64b4c99354aeb84695a4f
Source dataset
uspto-grants-1998_06
Patent number
US05760021

Reaction notes

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