Sodium Sulfite → 5alpha,6alpha-Epoxy-17beta-hydroxy-4,4-dimethylandrostan-3-one

HRID 1182872Notes

Reaction equation

HRID 1182872 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[OH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]2[C@H:19]3[C@H:29]([CH2:30][CH2:31][C@:14]12[CH3:15])[C@:27]1([CH3:28])[C:22]([C:23]([CH3:34])([CH3:33])[C:24](=[O:32])[CH2:25][CH2:26]1)=[CH:21][CH2:20]3.[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:9]1[C@H:21]2[CH2:20][C@@H:19]3[C@@H:29]([C@@:27]4([CH3:28])[CH2:26][CH2:25][C:24](=[O:32])[C:23]([CH3:34])([CH3:33])[C@:22]124)[CH2:30][CH2:31][C@@:14]1([CH3:15])[C@H:16]3[CH2:17][CH2:18][C@@H:13]1[OH:12]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 22415617beta-Hydroxy-4,4-dimethylandrost-5-en-3-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 866491775alpha,6alpha-Epoxy-17beta-hydroxy-4,4-dimethylandrostan-3-oneYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (1.17 g) was added to a stirred solution of 17β-hydroxy-4,4-dimethylandrost-5-en-3-one (1.00 g) in DCM (30 ml). After 8 h at RT, a 10% Na2SO3 aqueous solution was added. The mixture was neutralized by addition of 5% aqueous NaHCO3 solution and was extracted with DCM (3×100 ml). The combined organic extracts were washed with H2O, dried over Na2SO4, and evaporated to dryness. The mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 70/30) to give 5α,6α-epoxy-4,4-dimethyl-17β-hydroxyandrostan-3-one (230 mg, 23%).

Workup

  1. extractionwas extracted with DCM (3×100 ml)
  2. washThe combined organic extracts were washed with H2O
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 70/30)

Sources & evidence

ORD record
ord-2a74c8e44d6f41db9967689aaa71d450
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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