Sodium Hydroxide → 5-bromo-3-methyl-1'-(tetrahydro-2H-pyran-4-yl)-1',2',3',6'-tetrahydro-2,4'-bipyridine
Reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Br:15][C:16]1[CH:17]=[C:18]([CH3:28])[C:19]([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)=[N:20][CH:21]=1.[O:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1.[OH-].[Na+]>O1CCCC1.CCCCCC>[Br:15][C:16]1[CH:17]=[C:18]([CH3:28])[C:19]([C:22]2[CH2:23][CH2:24][N:25]([CH:32]3[CH2:33][CH2:34][O:29][CH2:30][CH2:31]3)[CH2:26][CH:27]=2)=[N:20][CH:21]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium triacetoxyborohydride (5.25 g) was added at room temperature to a solutions of 5-bromo-3-methyl-1′,2′,3′,6′-tetrahydro-2,4′-bipyridine (5.23 g) and tetrahydro-4H-pyran-4-one (2.07 g) in tetrahydrofuran (50 ml) and n-hexane (20 ml), and stirred at the same temperature. After completion of the reaction, 1N aqueous solution of sodium hydroxide was added under ice cooling and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) and washed with diethyl ether and n-hexane to give 5-bromo-3-methyl-1′-(tetrahydro-2H-pyran-4-yl)-1′,2′,3′,6′-tetrahydro-2,4′-bipyridine (3.1 g) as a pale yellow solid.
Workup
- additionwas added under ice cooling
- extractionextracted with chloroform
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol)
- washwashed with diethyl ether and n-hexane
Sources & evidence
- ORD record
- ord-aeb14af93d084ea5b67d2ec9ba2d2ef4
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150555B2
Reaction notes
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