Reaktion #319982

ord-2999bd1f158645bab610f3e064a88394

Reaktionsgleichung

CC(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](C(C)=O)CC[C@@H]32)C1
3α-Acetoxy-5α-pregnan-20-one
O=C1CCC(=O)N1Br
N-bromosuccinimide
O=C(OOC(=O)c1ccccc1)c1ccccc1
benzoyl peroxide
→
CC(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@]2(Br)C(C)=O)C1
3α-Acetoxy-17α-bromo-5α-pregnan-20-one

Edukte

—
16h
CC(=O)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](C(C)=O)CC[C@@H]32)C1
3α-Acetoxy-5α-pregnan-20-one
O=C1CCC(=O)N1Br
N-bromosuccinimide
O=C(OOC(=O)c1ccccc1)c1ccccc1
benzoyl peroxide

Reagenzien

Keine

Lösungsmittel

ClC(Cl)(Cl)Cl
carbon tetrachloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction mixture was cooled
  2. 2
    Filtrationfiltered
  3. 3
    Waschenwashed with sodium bisulfite, water, and brine
  4. 4
    Einengenconcentrated
  5. 5
    Sonstigeto give a crude reddish oil

Vorschrift

3α-Acetoxy-5α-pregnan-20-one (3 g, 360.5 g/m, 8.3 mmol), N-bromosuccinimide (2.7 g, 178 g/m, 15 mmol), and benzoyl peroxide (200 mg, 242 g/m, 0.83 mmol) dissolved in 50 ml of carbon tetrachloride were refluxed overnight (ca. 16h). The reaction mixture was cooled, filtered, and washed with sodium bisulfite, water, and brine, and then concentrated to give a crude reddish oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05591733uspto-grants-1997_01