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Sodium Hydroxide → 5-bromo-3-methyl-1'-(tetrahydro-2H-pyran-4-yl)-1',2',3',6'-tetrahydro-2,4'-bipyridine

HRID 1748531
Notes
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Reaction equation

HRID 1748531 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 866924815-Bromo-3-methyl-1',2',3',6'-tetrahydro-2,4'-bipyridine

Product 1

HCID 866924805-bromo-3-methyl-1'-(tetrahydro-2H-pyran-4-yl)-1',2',3',6'-tetrahydro-2,4'-bipyridineYield 44.5%

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

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

  1. additionwas added under ice cooling
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol)
  6. washwashed with diethyl ether and n-hexane

Sources & evidence

ORD record
ord-aeb14af93d084ea5b67d2ec9ba2d2ef4
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150555B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes