Hydrogen Peroxide → 4beta-Methyl-4alpha,5alpha-epoxy-17beta-hydroxyandrostan-3-one

HRID 1182891

Reaction equation

HRID 1182891 reaction equation
[CH3:1][C:2]1[C:18](=[O:19])[CH2:17][CH2:16][C@@:15]2([CH3:20])[C:3]=1[CH2:4][CH2:5][C@@H:6]1[C@@H:14]2[CH2:13][CH2:12][C@@:11]2([CH3:21])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[OH:22].OO.[O-:25]S([O-])=O.[Na+].[Na+].[Na+].[Cl-]>CO.[OH-].[Na+].O>[CH3:1][C@:2]12[O:25][C@:3]31[C@:15]([CH3:20])([CH2:16][CH2:17][C:18]2=[O:19])[C@@H:14]1[C@H:6]([C@H:7]2[C@@:11]([CH2:12][CH2:13]1)([CH3:21])[C@@H:10]([OH:22])[CH2:9][CH2:8]2)[CH2:5][CH2:4]3

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 24437Sodium SulfiteHCID 2365364-Methyltestosterone

Product 1

HCID 875533774beta-Methyl-4alpha,5alpha-epoxy-17beta-hydroxyandrostan-3-oneYield 25%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of 4-methyltestosterone (500 mg) in MeOH (60 ml) and NaOH 4N (2 ml) at 0° C., 30-32 wt. % H2O2 solution in water (2.0 ml) was added. The suspension was stirred at RT overnight. 10% aqueous Na2SO3 solution (5 ml) was cautiously added dropwise at 0° C. The mixture was saturated with NaCl and extracted three times with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (SiO2, toluene/tert-butyl methyl ether 80/20) to give 4β-methyl-4α,5α-epoxy-17β-hydroxyandrostan-3-one (130 mg, 25%).

Workup

  1. extractionextracted three times with EtOAc
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified by flash chromatography (SiO2, toluene/tert-butyl methyl ether 80/20)

Sources & evidence

ORD record
ord-39899e3e990b4265b77c08a315d184bb
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Linked notes

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