Hydrogen Peroxide → HCID 10967051, compound

HRID 1937130Notes

Reaction equation

HRID 1937130 reaction equation
[CH3:1][O:2][C@@H:3]1[C@H:7]2[CH2:8][C@@H:9]3[C@@H:14]([C:15](=[CH2:16])[C@H:6]2[C@H:5]([CH3:17])[O:4]1)[CH2:13][CH2:12][CH2:11][CH2:10]3.[OH2:18].OO.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[OH:18][CH2:16][C@H:15]1[C@@H:6]2[C@@H:7]([C@@H:3]([O:2][CH3:1])[O:4][C@H:5]2[CH3:17])[CH2:8][C@@H:9]2[C@@H:14]1[CH2:13][CH2:12][CH2:11][CH2:10]2.[OH:18][CH2:16][C@@H:15]1[C@@H:6]2[C@@H:7]([C@@H:3]([O:2][CH3:1])[O:4][C@H:5]2[CH3:17])[CH2:8][C@@H:9]2[C@@H:14]1[CH2:13][CH2:12][CH2:11][CH2:10]2

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 15427655HCID 15427655, compound

Product 2

HCID 10967051HCID 10967051, compoundYield 81%HCID 15427656HCID 15427656, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 99.8 mg(0.42 mmol) of (1S,3S,3aS,4aS,8aR,9aS)-1-methoxy-3-methyl-4-methylene-dodecahydronaphtho[2,3-c]furan in 10 ml of dehydrated tetrahydrofuran solution were added dropwise 633.4 μl (1.5 equivalents) of borane-tetrahydrofuran complex(1M) under cooling with ice and under an atmosphere of argon, and the mixture was stirred for 4.5 hours while raising temperature naturally. The reaction mixture was cooled with ice and 1 ml of water was added to stop the reaction. Then, 0.50 ml of 30% aqueous hydrogen peroxide and 0.50 ml of 10% aqueous solution of sodium hydroxide were added, which was stirred for 30 minutes. Solvent was distilled off and 20 ml of water were poured to the residue, which was extracted with methylene chloride(10 ml×3). The organic layer was dried over anhydrous magnesium sulfate, filtered and solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography(hexane:ethyl acetate=4:1, then 1:1) to obtain 86.7 mg of (1S,3S,3aR,4R,4aS,8aR,9aS)-4-hydroxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan (yield 81%) and 11.7 mg of (1S,3S,3aR,4S,4aS,8aR,9aS)-4-hydroxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan (yield 11%). (1S,3S,3aR,4R,4aS,8aR,9aS)-4-hydroxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan.

Workup

  1. temperatureunder cooling with ice and under an atmosphere of argon
  2. temperaturewhile raising temperature naturally
  3. additionwas added
  4. customthe reaction
  5. stirringwhich was stirred for 30 minutes
  6. distillationSolvent was distilled off
  7. addition20 ml of water were poured to the residue, which
  8. extractionwas extracted with methylene chloride(10 ml×3)
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. distillationsolvent was distilled off under reduced pressure
  12. customThe residue was purified by means of silica gel column chromatography(hexane

Sources & evidence

ORD record
ord-508c51b4735443399289748a274a5474
Source dataset
uspto-grants-2002_05
Patent number
US06392059B1

Reaction notes

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