Sodium Bicarbonate → HCID 86611031, Verbindung

HRID 2245919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245919
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2([C:33](OC)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1.[BH4-].[Li+].C([O-])(O)=O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2([CH2:33][OH:34])[CH2:29][CH2:30][CH2:31][CH2:32]2)=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 86611027HCID 86611027, Verbindung

Produkt 1

HCID 86611031HCID 86611031, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(1-methoxycarbonyl-cyclopent-1-yloxy)-benzyl]-benzene (0.15 g) in dry tetrahydrofuran (3 mL) chilled in an ice-bath is added lithium borohydride (8 mg). The reaction mixture is stirred at ambient temperature for 16 h. Aqueous NaHCO3 solution is added and the resulting mixture is extracted with ethyl acetate. The combined organic layers are dried (Na2SO4), the solvent is removed and the residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1).

Aufarbeitung

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. dry with materialThe combined organic layers are dried (Na2SO4)
  3. customthe solvent is removed
  4. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-07b6a907871e4969b777c803d0f0c99e
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683160B2

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