Hydrogen Peroxide → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17beta-(hydroxymethyl)androst-5-ene

HRID 1792222Notes

Reaction equation

HRID 1792222 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH2:15][C@@H:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C:20]2=[CH2:28])[CH2:12][C@@H:11]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C12BC(CCC1)CCC2.[OH-:46].[Na+].OO>CO>[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH2:15][C@@H:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH2:28][OH:46])[CH2:12][C@@H:11]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 696308851alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-methyleneandrost-5-ene

Product 1

HCID 696299821alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17beta-(hydroxymethyl)androst-5-ene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1α,3β-bis(tert-butyldimethylsilyloxy)-17-methyleneandrost-5-ene (30.3 g), was added 9-borabicyclo[3,3,1]nonane (0.5M solution in tetrahydrofuran, 228 ml) and reacted by stirring at room temperature for 4 hours. Under cooling with ice, a 3M sodium hydroxide solution (150 ml) and then a 30% hydrogen peroxide solution (150 ml) were added to the reaction mixture, followed by stirring at room temperature for 1 hour. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent, giving crude crystals (37.3 g). The crude crystals were mixed with methanol, stirred while under suspension, filtered and the thus obtained crystals were dried to give the titled compound (24.3 g).

Workup

  1. customreacted
  2. temperatureUnder cooling with ice
  3. stirringby stirring at room temperature for 1 hour
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customto remove the solvent
  9. customgiving crude crystals (37.3 g)
  10. stirringstirred while under suspension
  11. filtrationfiltered
  12. customthe thus obtained crystals were dried

Sources & evidence

ORD record
ord-72031b92e7964eb6b128206455f66ab4
Source dataset
uspto-grants-2006_07
Patent number
US07074777B2

Reaction notes

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