Hydrazine hydrate (1:1) → 16beta-Amino-3-methoxy-estra-1,3,5(10)-triene-17alpha-ol

HRID 1050284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1050284
[N:1]([C@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C@@H:5]1[OH:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)=[N+]=[N-].O.NN>[Ni].CO>[NH2:1][C@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C@@H:5]1[OH:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 2172340316beta-Azido-3-methoxy-estra-1,3,5(10)-triene-17alpha-ol

Produkt 1

HCID 1581915116beta-Amino-3-methoxy-estra-1,3,5(10)-triene-17alpha-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

1.0 g 16β-azido-3-methoxy-estra-1,3,5(10)-triene-17α-ol, 10 ml methanol, 2 ml 80% hydrazine hydrate and a spatula tip of Raney nickel are heated on a water bath for 15 min. After filtration, the Raney nickel is washed with methanol, subsequently wash fluid and filtrate are combined and methanol is removed by distillation under vacuum. The residue is recrystallized from methanol/ether. Yield: 0.8 g (87%), F=158-160° C.; [α]D+68° (pyridine).

Aufarbeitung

  1. filtrationAfter filtration
  2. washthe Raney nickel is washed with methanol, subsequently wash fluid and filtrate
  3. custommethanol is removed by distillation under vacuum
  4. customThe residue is recrystallized from methanol/ether
  5. customYield: 0.8 g (87%), F=158-160° C.

Quellen und Nachweise

ORD-Eintrag
ord-54457e27797349d3b8a5726d0be8ee0d
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382288B2

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