Reaktion #832828

ord-d77dd245542543d48b58558599e0f099

Reaktionsgleichung

CC(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(F)(F)C(C)(C)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](OC(C)=O)C1
[1α,3β]-24,24-difluorocholest-5-en-1,3,25-triol 1,3-diacetate
O=C([O-])O.[Na+]
sodium bicarbonate
CC1(C)C(=O)N(Br)C(=O)N1Br
1,3-dibromo-5,5-dimethylhydantoin
→
CC(=O)O[C@@H]1CC2=CC(Br)[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(F)(F)C(C)(C)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](OC(C)=O)C1
[1α,3β,7ξ]-7-bromo-24,24-difluorocholest-5-en-1,3,25-triol 1,3-diacetate

Edukte

CC(=O)O[C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(F)(F)C(C)(C)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)[C@@H](OC(C)=O)C1
[1α,3β]-24,24-difluorocholest-5-en-1,3,25-triol 1,3-diacetate
O=C([O-])O.[Na+]
sodium bicarbonate
CC1(C)C(=O)N(Br)C(=O)N1Br
1,3-dibromo-5,5-dimethylhydantoin

Reagenzien

Keine

Lösungsmittel

CCCCCC
hexane

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas heated
  2. 2
    Temperaturcooled
  3. 3
    FiltrationThe mixture was filtered
  4. 4
    Sonstigethe solids were triturated with hexane
  5. 5
    Filtrationfiltered
  6. 6
    SonstigeThe filtrates were evaporated to dryness

Vorschrift

A mixture of 1.05 g (0.0019 mol) of [1α,3β]-24,24-difluorocholest-5-en-1,3,25-triol 1,3-diacetate, 0.84 g of sodium bicarbonate, 0.357 g (0.0012 mol) of 1,3-dibromo-5,5-dimethylhydantoin and 40 mL of hexane was heated at reflux (80° C.) for 1 hr and cooled. The mixture was filtered and the solids were triturated with hexane and filtered. The filtrates were evaporated to dryness to yield [1α,3β,7ξ]-7-bromo-24,24-difluorocholest-5-en-1,3,25-triol 1,3-diacetate.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04599330uspto-grants-1986_07