1-Methyl-3-hydroxypyridine-2-one → 3-Hydroxy-1-methylpiperidin-2-one
Reaction equation
[OH:1][C:2]1[C:3](=[O:9])[N:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1>CO>[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([CH3:8])[C:3]1=[O:9]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 3-hydroxy-1-methyl-1H-pyridin-2-one (11.5 g, 91.91 mmol) and Ru/Al2O3 (2.5 g) in methanol (120 mL) was stirred under hydrogen (10 bar) in a 250-mL pressure reactor for 48 hr at 50° C. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to give the title compound (11.3 g, 90%) as a brown oil: 1H NMR (400 MHz, DMSO delta 3.85-3.82 (m, 1H), 3.28-3.18 (m, 2H), 2.79 (s, 3H), 1.98-1.92 (m, 1H), 1.87-1.81 (m, 1H), 1.75-1.69 (m, 1H), 1.64-1.55 (m, 1H).
Workup
- customThe catalyst was removed by filtration
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-6203f903b9b742ef99eead26410863ed
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901313B2
Reaction notes
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