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

HRID 1050284ノート

反応式

HRID 1050284 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-54457e27797349d3b8a5726d0be8ee0d
出典データセット
uspto-grants-2016_07
特許番号
US09382288B2

反応ノート

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