Sodium Hydroxide → HCID 86692463, compound

HRID 1748514

Reaction equation

HRID 1748514 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:16][CH:17]1[C:21](=O)[CH2:20][CH2:19][O:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]#[N:15])[CH2:9][CH2:10][N:11]([C@H:21]3[CH2:20][CH2:19][O:18][C@H:17]3[CH3:16])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 18522Dihydro-2-methyl-3(2H)-furanoneHCID 5049666Sodium triacetoxyborohydrideHCID 86692462HCID 86692462, compound

Product 1

HCID 86692463HCID 86692463, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4-(5-bromopyridin-2-yl)piperidine-4-carbonitrile (1.15 g) in toluene (14.4 ml), was added 2-methyltetrahydrofuran-3-one (526 mg), and then, sodium triacetoxyborohydride (1.37 g), and the mixture was stirred at room temperature for five hours. Water and 1N aqueous solution of sodium hydroxide were added to the reaction solution at 0° C., and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified with NH silica gel chromatography (n-hexane/ethyl acetate) to give cis-4-(5-bromopyridin-2-yl)-1-(2-methyltetrahydrofuran-3-yl)piperidine-4-carbonitrile (1.05 g) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with NH silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3fab7abd202c45af8fa18b53f3dd9013
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Linked notes

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