تفاعل #78036

ord-c8a352c0a05e41e0b43ed42a8dd9ad40

معادلة التفاعل

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

المتفاعلات

—
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

الكواشف

لا شيء

المذيبات

CC(=O)O
acetic acid

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06710039B1uspto-grants-2004_03