Reaktion #78036

ord-c8a352c0a05e41e0b43ed42a8dd9ad40

Reaktionsgleichung

C[C@]12CCC(=O)C3OC31CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)C[C@@H]3C[C@]312
17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one
CCOC(C)=O
ethyl acetate
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
O=S(=O)(O)O
sulfuric acid
→
C[C@]12CCC(=O)C(O)=C1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)C[C@@H]3C[C@]312
4,17β-Dihydroxy-14α,15α-methylene-androst-4-ene-3-one

Edukte

—
epoxide
C[C@]12CCC(=O)C3OC31CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)C[C@@H]3C[C@]312
17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one
CCOC(C)=O
ethyl acetate
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
O=S(=O)(O)O
sulfuric acid

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe organic phase is dried
  2. 2
    Einengenconcentrated
  3. 3
    workup.DISSOLUTIONThe residue is dissolved in 100 mL of methanol
  4. 4
    workup.ADDITIONtreated with 4 g of potassium hydroxide
  5. 5
    Temperaturrefluxed for 1 hour
  6. 6
    Temperaturcooled
  7. 7
    workup.ADDITIONAfter neutralization with 50% acetic acid, it is poured into 1 L of water
  8. 8
    Filtrationthe crystals are filtered off with suction, 4,17β-Dihydroxy-14α,15α-methylene-androst-4-ene-3-one being
  9. 9
    Sonstigeobtained

Vorschrift

An epoxide mixture (3.5 g), 17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one, (step 1) is dissolved in 50 mL of acetic acid, which contains 2% by volume of concentrated sulfuric acid. The solution is allowed to stand for 3 days at 10° C. After that, it is treated with 200 mL ethyl acetate and neutralized with sodium carbonate solution. The organic phase is dried and concentrated. The residue is dissolved in 100 mL of methanol, treated with 4 g of potassium hydroxide, refluxed for 1 hour and then cooled. After neutralization with 50% acetic acid, it is poured into 1 L of water and the crystals are filtered off with suction, 4,17β-Dihydroxy-14α,15α-methylene-androst-4-ene-3-one being obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06710039B1uspto-grants-2004_03