Reaktion #1270049

ord-583f53294cd44b129c8a7642c0e7f8b1

Reaktionsgleichung

C[C@]12CC[C@H]3[C@@H](CC(=O)C4C/C(=N\O[C@@H]5CCNC5)[C@H](F)C[C@@]43C)[C@@H]1CC[C@@H]2O.O=C(O)/C=C/C(=O)O
(E)-3-[3-(R)-pyrrolidinyl]oxyimino-2α-fluoro-17β-hydroxyandrostan-6-one fumarate
C[C@]12CC[C@H]3[C@@H](CC(=O)C4C/C(=N\O[C@@H]5CCNC5)[C@H](F)C[C@@]43C)[C@@H]1CC[C@@H]2O.O=C(O)/C=C/C(=O)O
(E)-3-[3-(R)-Pyrrolidinyl]oxyimino-2α-fluoro-17β-hydroxyandrostan-6-one fumarate
CON.Cl
methoxyamine hydrochloride
→
CO/N=C1\C[C@H]2[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]2[C@@]2(C)C[C@@H](F)/C(=N/O[C@@H]3CCNC3)CC12.O=C(O)/C=C/C(=O)O
title compound
CO/N=C1\C[C@H]2[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]2[C@@]2(C)C[C@@H](F)/C(=N/O[C@@H]3CCNC3)CC12.O=C(O)/C=C/C(=O)O
(E)-3-[3-(R)-Pyrrolidinyl]oxyimino-2α-fluoro-6-(E)-methoxyiminoandrostan-17β-ol fumarate

Edukte

C[C@]12CC[C@H]3[C@@H](CC(=O)C4C/C(=N\O[C@@H]5CCNC5)[C@H](F)C[C@@]43C)[C@@H]1CC[C@@H]2O.O=C(O)/C=C/C(=O)O
(E)-3-[3-(R)-pyrrolidinyl]oxyimino-2α-fluoro-17β-hydroxyandrostan-6-one fumarate
C[C@]12CC[C@H]3[C@@H](CC(=O)C4C/C(=N\O[C@@H]5CCNC5)[C@H](F)C[C@@]43C)[C@@H]1CC[C@@H]2O.O=C(O)/C=C/C(=O)O
(E)-3-[3-(R)-Pyrrolidinyl]oxyimino-2α-fluoro-17β-hydroxyandrostan-6-one fumarate
CON.Cl
methoxyamine hydrochloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter evaporation of the solvent the crude
  2. 2
    Sonstigereaction mixture
  3. 3
    Sonstigewas purified by flash chromatography (SiO2, CHCl3/MeOH/26% NH4OH 90/10/1)
  4. 4
    workup.ADDITIONTo the concentrated fractions, a stoichiometric amount of fumaric acid in MeOH was added
  5. 5
    WaschenThe resulting precipitate was rinsed with heptane
  6. 6
    Filtrationfiltered

Vorschrift

The title compound was obtained in 56% yield following the procedure described in Example 34 starting from (E)-3-[3-(R)-pyrrolidinyl]oxyimino-2α-fluoro-17β-hydroxyandrostan-6-one fumarate (Example 35, 72 mg) and methoxyamine hydrochloride (14 mg). After evaporation of the solvent the crude reaction mixture was purified by flash chromatography (SiO2, CHCl3/MeOH/26% NH4OH 90/10/1). To the concentrated fractions, a stoichiometric amount of fumaric acid in MeOH was added. The resulting precipitate was rinsed with heptane and filtered to give the title compound I-bk.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08664210B2uspto-grants-2014_03