Hydrogen Peroxide → HCID 86745917, compound

HRID 1885333Notes

Reaction equation

HRID 1885333 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[OH:5][CH2:6][C@@H:7]([CH3:28])[C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:27])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1.OO.[OH-:31].[Na+]>CO.ClCCl.O>[C:1]([OH:4])(=[O:3])[CH3:2].[O:31]1[C:15]23[C@:20]([CH3:21])([CH2:19][CH2:18][C:17](=[O:27])[CH:16]12)[C@@H:22]1[C@H:12]([C@H:11]2[C@:25]([CH3:26])([CH2:24][CH2:23]1)[C@@H:8]([C@H:7]([CH3:28])[CH2:6][OH:5])[CH2:9][CH2:10]2)[CH2:13][CH2:14]3

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86745918HCID 86745918, compound

Product 1

HCID 86745917HCID 86745917, compoundYield 122.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (20S)-21-hydroxy-20-methylpregn-4-en-3-one acetate (10.6 g, 28.3 mmole) in methanol (60 mL) and dichloromethane (15 mL) cooled to 15° C. in a cold water bath there was added 30% hydrogen peroxide (6.8 mL) and then, dropwise, a solution of sodium hydroxide (0.49 g) in water (3.2 mL). After 30 minutes, the cold bath was removed and the reaction was stirred for 4 hours at room temperature. The solvents were then removed under reduced pressure and the residue was dissolved in dichloromethane (300 mL) and extracted with brine (100 mL). The organic layer was separated, dried over magnesium sulfate, filtered and concentrated to a solid which was purified by flash chromatography on silica gel to give (20S)-4,5-epoxy-21-hydroxy-20-methylpregnan-3-one acetate (6.1 g, 55.6%) as a mixture of the 4α,5α- and 4,β5β-isomers.

Workup

  1. customthe cold bath was removed
  2. customThe solvents were then removed under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (300 mL)
  4. extractionextracted with brine (100 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a solid which
  9. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f85e3358e63b40298dd44cfe045f53df
Source dataset
uspto-grants-1992_09
Patent number
US05143909

Reaction notes

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