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

HRID 486309Notes

Reaction equation

HRID 486309 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-1757e9ed497b4d66bb64231c8f0245b2
Source dataset
uspto-grants-1994_03
Patent number
US05290948

Reaction notes

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