Sodium Hydroxide → HCID 86692486, Verbindung

HRID 1748535

Reaktionsgleichung

Reaktionsgleichung von HRID 1748535
[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

Komponenten

7

Edukt 4

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

Produkt 2

HCID 86692486HCID 86692486, VerbindungHCID 86692487HCID 86692487, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f291bff8ffc641889e21e04f986dabc8
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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