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

HRID 1050284Notes

Reaction equation

HRID 1050284 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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.

Sources & evidence

ORD record
ord-54457e27797349d3b8a5726d0be8ee0d
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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