HCID 13174066, compound → 6,7,8-Trihydroxy-1-(hydroxymethyl)-2-oxa-4-azabicyclo[3.3.1]nonan-3-one

HRID 543531Notes

Reaction equation

HRID 543531 reaction equation
Br[CH:2]1[CH:7]2[CH:8]([OH:13])[CH:9]([OH:12])[CH:10]([OH:11])[C:3]1([CH2:15][OH:16])[O:4][C:5](=[O:14])[NH:6]2.[H][H]>O.[Pd]>[OH:13][CH:8]1[CH:9]([OH:12])[CH:10]([OH:11])[C:3]2([CH2:15][OH:16])[CH2:2][CH:7]1[NH:6][C:5](=[O:14])[O:4]2

Participants

5

Reactant 2

HCID 13174066HCID 13174066, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131740726,7,8-Trihydroxy-1-(hydroxymethyl)-2-oxa-4-azabicyclo[3.3.1]nonan-3-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

In 100 ml of water is dissolved 2.0 g of 9-bromo-6,7,8-trihydroxy-1-hydroxymethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane, and 400 mg of palladium black is added to the solution, followed by stirring for 8 hours in a stream of hydrogen at room temperature. The catalyst is filtered off and washed with water. The filtrate and washings are combined, adjusted to pH 6 by adding a saturated aqueous solution of sodium hydrogen carbonate, and concentrated under reduced pressure. The residue is chromatographed on a column of 250 ml of MCI Gel CHP 20P (produced by Mitsubishi Chemical Ind., Ltd., Japan), followed by elution with water. The eluate is chromatographed on a column of activated carbon (250 ml), and the column is washed with water, followed by elution with a water-methanol gradient. The eluate containing the objective compound is concentrated under reduced pressure, and methanol is added to the residue, which is then allowed to stand overnight in a refrigerator to give crystals of 6,7,8-trihydroxy-1-hydroxymethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane. Yield of 780 mg.

Workup

  1. additionis added to the solution
  2. filtrationThe catalyst is filtered off
  3. washwashed with water
  4. additionby adding a saturated aqueous solution of sodium hydrogen carbonate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on a column of 250 ml of MCI Gel CHP 20P (produced by Mitsubishi Chemical Ind., Ltd., Japan)
  7. washfollowed by elution with water
  8. customThe eluate is chromatographed on a column of activated carbon (250 ml)
  9. washthe column is washed with water
  10. washfollowed by elution with a water-methanol gradient
  11. additionThe eluate containing the objective compound
  12. concentrationis concentrated under reduced pressure, and methanol
  13. additionis added to the residue, which

Sources & evidence

ORD record
ord-b49adf514fee4b64872e89b97f8ef0df
Source dataset
uspto-grants-1984_05
Patent number
US04446319

Reaction notes

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