Sodium Hydroxide → HCID 86692463, Verbindung

HRID 1748514

Reaktionsgleichung

Reaktionsgleichung von HRID 1748514
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 86692463HCID 86692463, VerbindungAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3fab7abd202c45af8fa18b53f3dd9013
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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