Triacetoxyperiodinane → HCID 15427654, compound

HRID 1937127Notes

Reaction equation

HRID 1937127 reaction equation
[OH:1][C@H:2]1[C@@H:14]2[C@@H:10]([C@@H:11]([O:16][CH3:17])[O:12][C@H:13]2[CH3:15])[CH2:9][C@@H:8]2[C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7]2.C(=O)([O-])O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:17][O:16][C@@H:11]1[C@H:10]2[CH2:9][C@@H:8]3[C@@H:3]([C:2](=[O:1])[C@H:14]2[C@H:13]([CH3:15])[O:12]1)[CH2:4][CH2:5][CH2:6][CH2:7]3

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 10922673HCID 10922673, compound

Product 1

HCID 15427654HCID 15427654, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.23 g(5.12 mmol) of (1S,3S,3aS,4R,4aS,8aR,9aS)-4-hydroxy-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan and 3.26 g of sodium hydrogencarbonate in 100 ml of methylene chloride suspension were added 3.26 g(1.5 equivalents) of Dess-Martin reagent under stirring and cooling with ice, and the mixture was stirred for 1 hour at room temperature. After 6.35 g of sodium thiosulfate 5-hydrate and 50 ml of saturated aqueous solution of sodium hydrogencarbonate were added to the reaction mixture and stirred, two layers were separated and extraction with methylene chloride(5 ml×3) was performed from aqueous layer. The organic layers were dried over anhydrous magnesium sulfate, filtered and solvent was distilled off. The residue was purified by means of silica gel column chromatography(hexane:ethyl acetate=4:1) to obtain 1.18 g of (1S,3S,3aR,4aS,8aR,9aS)-1-methoxy-3-methyl-4-oxo-dodecahydronaphtho[2,3-c]furan (yield 97%).

Workup

  1. temperaturecooling with ice
  2. stirringthe mixture was stirred for 1 hour at room temperature
  3. stirringstirred
  4. customtwo layers were separated
  5. extractionextraction with methylene chloride(5 ml×3)
  6. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationsolvent was distilled off
  9. customThe residue was purified by means of silica gel column chromatography(hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-8f68b33504c440aeb19d1faae449eec8
Source dataset
uspto-grants-2002_05
Patent number
US06392059B1

Reaction notes

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