HCID 18648380, compound → Deoxynojirimycin

HRID 1735180Notes

Reaction equation

HRID 1735180 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([OH:23])[C@@H:12]([CH2:24][O:25]CC2C=CC=CC=2)[NH:11][CH2:10]1)C1C=CC=CC=1>CO.C(O)=O.[Pd]>[NH:11]1[C@H:12]([CH2:24][OH:25])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@@H:9]([OH:8])[CH2:10]1

Participants

5

Reactant 1

HCID 18648380HCID 18648380, compound

Product 1

HCID 29435DeoxynojirimycinYield 80%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

2,3,6-Tri-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol (0.2 g, 0.46 mmol) is dissolved in a 9:1 mixture of methanol and formic acid (10 ml) under an inert atmosphere and palladium 10% on charcoal (0.4 g) is added. The mixture is stirred overnight at room temperature. The catalyst is removed by filtration. The solvents are evaporated under reduced pressure. The residue is dissolved in methanol and the solution is filtered through a membrane (Millex-SR 0.5 μM). Evaporation of solvent gives a sticky solid which is further triturated in ethanol to give the expected 1,5-dideoxy-1,5-imino-D-glucitol as a beige powder (60 mg, 80%).

Workup

  1. additionis added
  2. customThe catalyst is removed by filtration
  3. customThe solvents are evaporated under reduced pressure
  4. dissolutionThe residue is dissolved in methanol
  5. filtrationthe solution is filtered through a membrane (Millex-SR 0.5 μM)
  6. customEvaporation of solvent
  7. customgives a sticky solid which
  8. customis further triturated in ethanol

Sources & evidence

ORD record
ord-7b75d4b3b99f49c3b937c1a5f98c1e56
Source dataset
uspto-grants-1996_07
Patent number
US05536732

Reaction notes

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