Sodium sulfate decahydrate → (6-(2-fluoro-5-methoxyphenyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)pyridin-3-yl)methanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[C:25]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)=[CH:24][C:19]([C:20](OC)=[O:21])=[CH:18][N:17]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[N:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:24][C:25]=1[O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Under a nitrogen atmosphere, to a suspension of lithium aluminum hydride (74 mg) in THF (9.7 mL) was added dropwise a solution of methyl 6-(2-fluoro-5-methoxyphenyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)nicotinate (466 mg) in THF (3.2 ml) at 0° C., and the mixture was stirred for 1 hr. Sodium sulfate decahydrate was added by small portions, and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (193 mg) as a colorless gummy substance.
Workup
- stirringthe mixture was further stirred at room temperature for 1 hr
- filtrationThe reaction mixture was filtered
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-8a1d6caef44f4bbfb2460705192ffcb8
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181186B2
Reaction notes
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