反応 #78036

ord-c8a352c0a05e41e0b43ed42a8dd9ad40

反応方程式

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

反応物

—
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

試薬

なし

溶媒

CC(=O)O
acetic acid

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他The organic phase is dried
  2. 2
    濃縮concentrated
  3. 3
    workup.DISSOLUTIONThe residue is dissolved in 100 mL of methanol
  4. 4
    workup.ADDITIONtreated with 4 g of potassium hydroxide
  5. 5
    温度refluxed for 1 hour
  6. 6
    温度cooled
  7. 7
    workup.ADDITIONAfter neutralization with 50% acetic acid, it is poured into 1 L of water
  8. 8
    ろ過the crystals are filtered off with suction, 4,17β-Dihydroxy-14α,15α-methylene-androst-4-ene-3-one being
  9. 9
    その他obtained

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US06710039B1uspto-grants-2004_03