Sodium Hydroxide → HCID 86692486, compound

HRID 1748535

Reaction equation

HRID 1748535 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)=[N:6][CH:7]=1.[CH3:15][CH:16]1[C:20](=O)[CH2:19][CH2:18][O:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([C:8]2[CH2:9][CH2:10][N:11]([C@H:20]3[CH2:19][CH2:18][O:17][C@H:16]3[CH3:15])[CH2:12][CH:13]=2)=[N:6][CH:7]=1.[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([C:8]2[CH2:9][CH2:10][N:11]([C@@H:20]3[CH2:19][CH2:18][O:17][C@H:16]3[CH3:15])[CH2:12][CH:13]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 18522Dihydro-2-methyl-3(2H)-furanoneHCID 5049666Sodium triacetoxyborohydrideHCID 86692481HCID 86692481, compound

Product 2

HCID 86692486HCID 86692486, compoundHCID 86692487HCID 86692487, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-3-methyl-1′,2′,3′,6′-tetrahydro-2,4′-bipyridine (2.26 g) described in Reference Example 109 (2) and 2-methyltetrahydrofuran-3-one (1.1 ml) in dichloromethane (25 ml) was added sodium triacetoxyborohydride (2.77 g), and stirred at room temperature for 6 hours. To the reaction solution was added 1 N aqueous solution of sodium hydroxide, and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give cis-4-(5-bromo-3-methyl-pyridin-2-yl)-1-(2-methyltetrahydrofuran-3-yl)-1,2,3,6-tetrahydropyridine (2.43 g) and trans-4-(5-bromo-3-methylpyridin-2-yl)-1-(2-methyltetrahydrofuran-3-yl)-1,2,3,6-tetrahydropyridine (193 mg) as brown oils respectively. MS (ESI) m/z: 337, 339 (M+H)+.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f291bff8ffc641889e21e04f986dabc8
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Linked notes

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