Methyl 5-hydroxypyridine-3-carboxylate → Methyl 5-hydroxypiperidine-3-carboxylate
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
Product 1
Reagents, catalysts & solvents 2
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
- temperatureto cool
- filtrationfiltered through a microfiber
- filtrationfilter paper
- concentrationconcentrated in vacuo which
- customafforded a viscous colorless residue
- customThe residue was azeotroped with toluene
- customdried which
Sources & evidence
- ORD record
- ord-530ef735440e4c5b90be4f230f99feca
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518952B2
Reaction notes
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