Reaktion #1926098

ord-0244ffd4548a480fafbcb757cd3b173c

Reaktionsgleichung

CCN(CC)CC
triethylamine
C[C@]12C[C@H](F)[C@@H]3c4ccc(O)cc4C[C@@H](CCCCCBr)[C@H]3[C@@H]1CCC2=O
11β-fluoro-7α-(5-bromopentyl)-3-hydroxyestra-1,3,5(10)-trien-17-one
C1=COCCC1
3,4-dihydropyran
Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulphonic acid hydrate
→
C[C@]12C[C@H](F)[C@@H]3c4ccc(OC5CCCCO5)cc4C[C@@H](CCCCCBr)[C@H]3[C@@H]1CCC2=O
11β-fluoro-7α-(5-bromopentyl)-3-(tetrahydropyran-2-yloxy)oestra-1,3,5(10)-trien-17-one

Edukte

CCN(CC)CC
triethylamine
C[C@]12C[C@H](F)[C@@H]3c4ccc(O)cc4C[C@@H](CCCCCBr)[C@H]3[C@@H]1CCC2=O
11β-fluoro-7α-(5-bromopentyl)-3-hydroxyestra-1,3,5(10)-trien-17-one
C1=COCCC1
3,4-dihydropyran
Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulphonic acid hydrate

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
ethyl acetate
C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with saturated sodium chloride solution until neutral and
  2. 2
    Trocknendried over sodium sulphate

Vorschrift

8.4 g of 11β-fluoro-7α-(5-bromopentyl)-3-hydroxyestra-1,3,5(10)-trien-17-one in 90 ml of tetrahydrofuran are allowed to react at room temperature with 9.0 ml of 3,4-dihydropyran and 805 mg of p-toluenesulphonic acid hydrate. After 7 h, 1 ml of triethylamine is added, and the mixture is diluted with ethyl acetate, washed with saturated sodium chloride solution until neutral and dried over sodium sulphate. Chromatography on silica gel using a hexane-ethyl acetate gradient affords 7.6 g of 11β-fluoro-7α-(5-bromopentyl)-3-(tetrahydropyran-2-yloxy)oestra-1,3,5(10)-trien-17-one as a foam.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06677324B1uspto-grants-2004_01