HCID 21789509, compound → HCID 21789511, compound

HRID 2397480Notes

Reaction equation

HRID 2397480 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C@H:8]2[O:28][C@H:27]([CH2:29][O:30]CC3C=CC=CC=3)[C@@H:18]([O:19]CC3C=CC=CC=3)[C@@H:9]2[O:10]CC2C=CC=CC=2)[N:3]=1>CO.Cl.[Pd]>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C@H:8]2[O:28][C@H:27]([CH2:29][OH:30])[C@@H:18]([OH:19])[C@@H:9]2[OH:10])[N:3]=1

Participants

5

Reactant 1

HCID 21789509HCID 21789509, compound

Product 1

HCID 21789511HCID 21789511, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

1 g of Pd-black is pre-hydrogenated for 2 hours in 25 ml of absolute methanol. Then 3 g (6.0 mmoles) of 3,5-dimethyl-1-(2,3,5-tri-O-benzyl-α-D-arabinofuranosyl)pyrazole are added in 25 ml of absolute methanol and 0.8 ml of concentrated hydrochloric acid. Hydrogenation is carried out for 20 hours at room temperature. Then the catalyst is filtered off and the reaction mixture is fed onto a column with 20 g of amberlite IRA-402 in the OH⃝ -form for neutralisation and is eluated with methanol. After drawing off the solvent, a colorless syrup (which cannot be used for crystallization) remains. For purification therefore the substance is only dissolved in methanol and boiled up with active charcoal. The preparation is then thoroughly dried with a continuously running oil pump. Yield: 1.35 g (99%); Rf (silica gel, acetone): 0.5.

Workup

  1. filtrationThen the catalyst is filtered off
  2. customa colorless syrup (which cannot be used for crystallization)
  3. customFor purification
  4. dissolutionthe substance is only dissolved in methanol
  5. customThe preparation is then thoroughly dried with

Sources & evidence

ORD record
ord-a19f54831eee4d19888f9529d5be5b92
Source dataset
uspto-grants-1977_05
Patent number
US04021542

Reaction notes

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