Hydrogen Peroxide → HCID 86745917, compound

HRID 2082411Notes

Reaction equation

HRID 2082411 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 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 4α,5α- and 4β,5β-isomers.

Workup

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

Sources & evidence

ORD record
ord-e098fe043d714cc6b032cad10e531820
Source dataset
uspto-grants-1993_02
Patent number
US05189032

Reaction notes

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