HCID 11074968, compound → HCID 12011994, compound

HRID 1937125Notes

Reaction equation

HRID 1937125 reaction equation
[OH:1][C@H:2]1[C@@H:14]2[C@@H:10]([C:11](=[O:16])[O:12][C@H:13]2[CH3:15])[CH:9]=[C:8]2[C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7]2>C(O)C.[Pt]=O>[OH:1][C@H:2]1[C@@H:14]2[C@@H:10]([C:11](=[O:16])[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

Participants

4

Reactant 1

HCID 11074968HCID 11074968, compound

Product 1

HCID 12011994HCID 12011994, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To 375.1 mg(1.69 mmol) of (3S,3aS,4R,4aS,9aS)-4-hydroxy-3-methyl-3a,4,4a,5,6,7,8,9a-octahydronaphtho[2,3-c]furan-1(3H)-one in 5 ml of ethanol solution were added 40.0 mg(10% by weight) of platinum oxide, and catalytic reduction was conducted at ambient temperature under 98.1 Kpa. After stirring for 16 hours, the reaction mixture was filtered through celite and the residue was washed using 20 ml of ethyl acetate. Combined organic layers were distilled off under reduced pressure and the residue was purified by means of silica gel column chromtography(methylene chloride:ethyl acetate=4:1) to obtain 363.7 mg of (3S,3aS,4R,4aS,8aR,9aS)-4-hydroxy-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one (yield 96%).

Workup

  1. customwas conducted at ambient temperature under 98.1 Kpa
  2. filtrationthe reaction mixture was filtered through celite
  3. washthe residue was washed
  4. distillationCombined organic layers were distilled off under reduced pressure
  5. customthe residue was purified by means of silica gel column chromtography(methylene chloride:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-ed99694a32bf4f3199fdecb508d9c81e
Source dataset
uspto-grants-2002_05
Patent number
US06392059B1

Reaction notes

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