Sodium Chloride → 11beta-Fluoro-7alpha-{5-[(3,4,4,5,5,5-hexafluoropent-2-enyl)methyl-amino]pentyl}oestra-1,3,5(10)-triene-3,17beta-diol

HRID 1838915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1838915
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:39])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH:29]=[C:30]([F:38])[C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33])[CH3:27].[BH4-].[Na+].[Cl-].[Na+]>CO>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:39])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH:29]=[C:30]([F:38])[C:31]([F:36])([F:37])[C:32]([F:33])([F:34])[F:35])[CH3:27]

Komponenten

5

Edukt 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 86587645HCID 86587645, Verbindung

Produkt 1

HCID 8658764611beta-Fluoro-7alpha-{5-[(3,4,4,5,5,5-hexafluoropent-2-enyl)methyl-amino]pentyl}oestra-1,3,5(10)-triene-3,17beta-diolAusbeute 12,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.86 g of 11β-fluoro-7α-{5-[(3,4,4,5,5,5-hexafluoro-pent-2-enyl)methylamino]pentyl}-3-hydroxyestra-1,3,5(10)-trien-17-one are dissolved in 15 ml of methanol and cautiously treated with 222 mg of sodium borohydride. After stirring at room temperature for 15 minutes, the mixture is added to saturated sodium chloride solution, extracted with methylene chloride, dried over magnesium sulphate and concentrated in vacuo. After chromatographing the crude product on silica gel using a hexane-ethyl acetate and an ethyl acetate-acetone gradient, 241 mg of 11β-fluoro-7α-{5-[(3,4,4,5,5,5-hexafluoropent-2-enyl)methyl-amino]pentyl}oestra-1,3,5(10)-triene-3,17β-diol of melting point 122° C. are obtained, [α]D=+47° (c=0.5 in CHCl3)

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7f559eab67d34012afa3fd7db6a9fc17
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677324B1

Notizen zur Reaktion

Wird geladen…