Sodium Hydroxide → 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridin-3-ylmethanol
Reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH:7]([C:9]1[N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]2=[N:11][CH:10]=1)=[O:8].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.O>[N:11]1[CH:10]=[C:9]([CH2:7][OH:8])[N:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]=12Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of aluminum lithium hydride (0.40 g) in THF (30 ml), 3-formyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (1.48 g) in. THF (50 ml) was added dropwise at 0° C. The mixture was stirred for 1 hour at 0° C., and water (0.4 ml), 15% aqueous solution of sodium hydroxide (0.4 ml) and water (1.2 ml) were added dropwise to the mixture. The mixture was stirred at room temperature for 18 hours, magnesium sulfate was added to the mixture, and the precipitates were removed by filtration. The solvent was concentrated under reduced pressure, and the precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether, to give 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-methanol (1.24 g) as colorless crystals.
Workup
- stirringThe mixture was stirred at room temperature for 18 hours
- customthe precipitates were removed by filtration
- concentrationThe solvent was concentrated under reduced pressure
- filtrationthe precipitated crystals were collected by filtration
- washThe crystals were washed with diisopropyl ether
Sources & evidence
- ORD record
- ord-60de4f8d0d5f4457afae3cc8e78afa40
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07262185B2
Reaction notes
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