Reaktion #684162

ord-0d337fc45ffe4f7aa9eb54d9cc934138

Reaktionsgleichung

CC(=O)OCC(=O)[C@H]1[C@@H]2C[C@@H]2[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C
3β-hydroxy-21-acetoxy-15α,16α-methylene-5-pregnen-20-one
O=C([O-])O.[K+]
potassium bicarbonate
F
hydrogen fluoride
O=C1CCC(=O)N1Br
N-bromosuccinimide
→
CC(=O)OCC(=O)[C@H]1[C@@H]2C[C@@H]2[C@H]2[C@@H]3C[C@@H](F)[C@@]4(Br)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C
6β-fluoro-5-bromo-3β-hydroxy-21-acetoxy-15α,16α-methylene-5α-pregnan-20-one

Edukte

CC(=O)OCC(=O)[C@H]1[C@@H]2C[C@@H]2[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C
3β-hydroxy-21-acetoxy-15α,16α-methylene-5-pregnen-20-one
O=C([O-])O.[K+]
potassium bicarbonate
—
liquid
F
hydrogen fluoride
O=C1CCC(=O)N1Br
N-bromosuccinimide

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride
CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Temperatur
-15°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with methylene chloride
  2. 2
    SonstigeAfter drying
  3. 3
    Sonstigeevaporation, 700 mg

Vorschrift

2.5 ml of liquid hydrogen fluoride is added to 2.5 ml. of dimethylformamide cooled to -40° C. The reaction mixture is combined with 250 mg. of N-bromosuccinimide, and then 500 mg. of 3β-hydroxy-21-acetoxy-15α,16α-methylene-5-pregnen-20-one, dissolved in 5 ml. of methylene chloride, is introduced into this reaction mixture. The latter is agitated for 5 minutes at -15° C., poured into saturated potassium bicarbonate solution, and extracted with methylene chloride. After drying and evaporation, 700 mg. of crude 6β-fluoro-5-bromo-3β-hydroxy-21-acetoxy-15α,16α-methylene-5α-pregnan-20-one is obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04012510uspto-grants-1977_03