Methyl 5-hydroxypyridine-3-carboxylate → Methyl 5-hydroxypiperidine-3-carboxylate

HRID 1896212Notes

Reaction equation

HRID 1896212 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=1>[Rh].C(O)(=O)C>[CH3:11][O:10][C:8]([CH:4]1[CH2:3][CH:2]([OH:1])[CH2:7][NH:6][CH2:5]1)=[O:9]

Participants

4

Reactant 1

HCID 354317Methyl 5-hydroxypyridine-3-carboxylate

Product 1

HCID 49759515Methyl 5-hydroxypiperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 176Acetic AcidSolvent

Procedure

Methyl 5-hydroxypyridine-3-carboxylate (22 g, 140 mmol), acetic acid (250 mL) and rhodium on alumina (2.2 g, 21 mmol) were added to a 1 L reactor. The mixture was hydrogenated at 200 psi and 50° C. for 18 h. The reaction was allowed to cool, then filtered through a microfiber filter paper, and concentrated in vacuo which afforded a viscous colorless residue. The residue was azeotroped with toluene and dried which gave the title compound IIIa (25.4 g, 78%).

Workup

  1. temperatureto cool
  2. filtrationfiltered through a microfiber
  3. filtrationfilter paper
  4. concentrationconcentrated in vacuo which
  5. customafforded a viscous colorless residue
  6. customThe residue was azeotroped with toluene
  7. customdried which

Sources & evidence

ORD record
ord-530ef735440e4c5b90be4f230f99feca
Source dataset
uspto-grants-2013_08
Patent number
US08518952B2

Reaction notes

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