Reacción #78036

ord-c8a352c0a05e41e0b43ed42a8dd9ad40

Ecuación de reacción

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

Reactantes

—
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

Reactivos

Ninguno

Disolventes

CC(=O)O
acetic acid

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06710039B1uspto-grants-2004_03