Hydrogen Peroxide → HCID 86738157, compound

HRID 1659837Notes

Reaction equation

HRID 1659837 reaction equation
[OH:1][C@@H:2]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]2)[CH:10]=[CH:9]3)[CH2:6][CH2:5]1)[CH3:3].[OH-:24].[Na+].OO.O>CO>[O:24]1[C@H:14]2[C:13](=[O:23])[CH:12]=[C:11]3[C@:16]([CH3:17])([C@@H:15]12)[C@@H:18]1[C@H:8]([C@H:7]2[C@:21]([CH3:22])([CH2:20][CH2:19]1)[C@@H:4]([C@H:2]([OH:1])[CH3:3])[CH2:5][CH2:6]2)[CH:9]=[CH:10]3

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 54022890HCID 54022890, compound

Product 1

HCID 86738157HCID 86738157, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.79 g (8.92 mmol) of (20R)-20-hydroxy-pregna-1,4,6-trien-3-one in 27 ml of methanol is treated with 0.83 ml of 10% methanolic sodium hydroxide, cooled to 0° C., and 5.4 ml of 30% hydrogen peroxide solution are added dropwise during 10 minutes with stirring. The solution is stirred at 0° C. for 45 minutes and then at room temperature for 3 hours. The suspension formed is treated with a total of 60 ml of water in portions, cooled to 0° C. and excess peroxide is destroyed by the addition of sodium hydrogen sulphite solution. The mixture is freed from methanol in a water-jet vacuum and the residue is extracted with ethyl acetate. The extract is washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated. Chromatography of the residue on 80 g of silica gel with hexane/ether (1:1) gives 1.77 g (60.4%) of uniform (20R)-1α,2α -epoxy-20-hydroxy-pregna-4,6-dien-3-one in the form of colourless crystals. The analytical sample is obtained by recrystallisation from methylene chloride/ether; melting point 206°-207° C., [α]D25 =+231.6° (c=0.5 in chloroform); UV (ethanol): λmax 292 nm (ε=21050).

Workup

  1. stirringThe solution is stirred at 0° C. for 45 minutes
  2. customThe suspension formed
  3. temperaturecooled to 0° C.
  4. customexcess peroxide is destroyed by the addition of sodium hydrogen sulphite solution
  5. extractionthe residue is extracted with ethyl acetate
  6. washThe extract is washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-5b0105627cb7449198c597d53e85d1f7
Source dataset
uspto-grants-1981_12
Patent number
US04305881

Reaction notes

Loading…