Reaktion #1461966

ord-724f80660c814d04928d93522ddc55a4

Reaktionsgleichung

CC1([C@H]2CC[C@]3(O)[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4C[C@@H](O)[C@]23C)OCCO1
ethylenedioxypregnene
CC1([C@H]2CC[C@]3(O)[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4C[C@@H](O)[C@]23C)OCCO1
3β,12β,14β-Trihydroxy-20,20-ethylenedioxypregn-5-ene
→
CC[C@H]1CC[C@]2(O)[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3C[C@@H](O)[C@]12C
trihydroxy steroid
Ausbeute 93.4%
CC[C@H]1CC[C@]2(O)[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3C[C@@H](O)[C@]12C
3β,12β,14β-Trihydroxy-pregn-5-ene
Ausbeute 93.4%

Edukte

CC1([C@H]2CC[C@]3(O)[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4C[C@@H](O)[C@]23C)OCCO1
ethylenedioxypregnene
CC1([C@H]2CC[C@]3(O)[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4C[C@@H](O)[C@]23C)OCCO1
3β,12β,14β-Trihydroxy-20,20-ethylenedioxypregn-5-ene

Reagenzien

Keine

Lösungsmittel

CC(=O)O
acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Trocknenwater which after freeze drying

Vorschrift

The ethylenedioxypregnene (25) (250 mg, 0.64 mmol) is dissolved in acetic acid (13.4 ml) and water which after freeze drying affords the trihydroxy steroid (15) (200 mg, 89%), m.p.: 228°–235° C. (lit. 225°–235° C.), M+348, [αD]20 +35° (lit [αD]20+29°).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07166611B2uspto-grants-2007_01