N-Methyl-D-glucamine → 1-Deoxy-1-[[(4-ethenylphenyl)methyl]methylamino]-D-glucitol

HRID 1453414Notes

Reaction equation

HRID 1453414 reaction equation
[CH3:1][NH:2][CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5].[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1)=[CH2:15].C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH:14]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:2]([CH3:1])[CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5])=[CH:18][CH:17]=1)=[CH2:15]

Participants

5

Reactant 3

HCID 8567N-Methyl-D-glucamineHCID 10340Sodium CarbonateHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 688699661-Deoxy-1-[[(4-ethenylphenyl)methyl]methylamino]-D-glucitolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
4 °C

Procedure

N-Methylglucamine (9.76 g, 50 mmol) was dissolved in hot methanol (200 mL), whereupon 4-vinylbenzylchloride (7.63 g, 50 mmol) and sodium carbonate (6 g) were added to the reaction. The mixture was allowed to reflux overnight. The solution was filtered, the methanol was removed, the residue taken up in hot chloroform and filtered. A precipitate formed in the eluent, which was heated until all solids dissolved and the solution was allowed to cool to 4° C. Filtration gave 14 g (90% yield) of white powder. 1H-NMR (90 MHz, DMSO-d6, δ): 7.33-7.28 (d, 4H); 6.86-6.83 (dd, 1H); 5.85-5.64 (d, 1H); 5.25-5.12 (d, 1H); 2.11 (s, 3h).

Workup

  1. temperatureto reflux overnight
  2. filtrationThe solution was filtered
  3. customthe methanol was removed
  4. filtrationfiltered
  5. customA precipitate formed in the eluent, which
  6. temperaturewas heated until all solids
  7. dissolutiondissolved
  8. filtrationFiltration

Sources & evidence

ORD record
ord-a19564c99efe40bd9ae3ef071240d886
Source dataset
uspto-grants-2009_01
Patent number
US07476316B2

Reaction notes

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