Reaktion #354813

ord-f81931cf82a14d72823fe29458c47bde

Reaktionsgleichung

COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC=CC[C@]4(C)[C@H]3C(=O)C[C@]12C
17β-Methoxycarbonyl-5α-androst-2-en-11-one
O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid
→
COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H]5O[C@@H]5C[C@]4(C)[C@H]3C(=O)C[C@]12C
2α,3α-Epoxy-17β-methoxycarbonyl-5α-androstan-11-one

Edukte

COC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC=CC[C@]4(C)[C@H]3C(=O)C[C@]12C
17β-Methoxycarbonyl-5α-androst-2-en-11-one
O=C(OO)c1cccc(Cl)c1
m-chloroperbenzoic acid

Reagenzien

Keine

Lösungsmittel

ClC(Cl)Cl
chloroform
ClC(Cl)Cl
chloroform

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with 2% aqueous potassium hydrogen carbonate
  2. 2
    Trocknendried (MgSO4)
  3. 3
    Sonstigeevaporated to a gum
  4. 4
    SonstigeCrystallisation from ethyl acetate/light petroleum afforded pure title compound
  5. 5
    Sonstige[α]D + 74.2°

Vorschrift

17β-Methoxycarbonyl-5α-androst-2-en-11-one (6.63 g.) and m-chloroperbenzoic acid (4.84 g.) were stirred with chloroform (115 ml.) for 16 hours. The solution was diluted with chloroform, washed with 2% aqueous potassium hydrogen carbonate, dried (MgSO4) and evaporated to a gum. Crystallisation from ethyl acetate/light petroleum afforded pure title compound. (1.64 g.) as colourless rods; m.p. 140°-145°; [α]D + 74.2°.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US03943124uspto-grants-1976_03