Diethyl Ether → N-2-(4-Fluorophenoxy)ethyl-2,5-Anhydro-2,5-imino-D-glucitol

HRID 486309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486309
[NH:1]1[C@:9]2([CH2:11][OH:12])[O:10][C@:2]1([C@H:5]([C@@H:7]2[OH:8])[OH:6])[CH2:3][OH:4].[F:13][C:14]1[CH:23]=[CH:22][C:17]([O:18][CH2:19][CH2:20]Br)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].C(OCC)C>CN(C)C=O>[F:13][C:14]1[CH:23]=[CH:22][C:17]([O:18][CH2:19][CH2:20][N:1]2[C@:9]3([CH2:11][OH:12])[O:10][C@:2]2([C@H:5]([C@@H:7]3[OH:8])[OH:6])[CH2:3][OH:4])=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 20641711-(2-Bromoethoxy)-4-fluorobenzeneHCID 68719483(1S,2S,3S,4R)-1,4-bis(hydroxymethyl)-5-oxa-6-azabicyclo[2.1.1]hexane-2,3-diol

Produkt 1

HCID 131718343N-2-(4-Fluorophenoxy)ethyl-2,5-Anhydro-2,5-imino-D-glucitol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of a compound Formula XIV (2.60 g, 0.0159 mol), 2-(4-fluorophenoxy)ethyl bromide (3.70 g, 0.0169 mol), and Na2CO3 (1.86 g, 0.0175 mol) in 11 mL of dimethylformamide was heated at 85° C. for 8 h. The solution was cooled, then treated with 250 mL of ethyl ether portion wise, and the solvent was removed. The resultant residue was diluted with chloroform, filtered, and concentrated. This crude material was chromatographed on a Waters Prep-500 HPLC (88:11:1, CHCl3 /MEOH/NH4OH) to give the product, which was recrystallized from EtOAc/hexane (3.49 g, 73%), mp 96°-98° C. (corrected). 1H NMR supported the assigned structure.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customthe solvent was removed
  3. additionThe resultant residue was diluted with chloroform
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis crude material was chromatographed on a Waters Prep-500 HPLC (88:11:1, CHCl3 /MEOH/NH4OH)
  7. customto give the product, which
  8. customwas recrystallized from EtOAc/hexane (3.49 g, 73%), mp 96°-98° C. (corrected)

Quellen und Nachweise

ORD-Eintrag
ord-1757e9ed497b4d66bb64231c8f0245b2
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290948

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