HCID 18648380, compound → Deoxynojirimycin

HRID 1655999Notes

Reaction equation

HRID 1655999 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-65540079f3554348bc0530e78d7ff577
Source dataset
uspto-grants-1993_10
Patent number
US05252587

Reaction notes

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