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

HRID 1050284노트

반응식

HRID 1050284 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-54457e27797349d3b8a5726d0be8ee0d
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382288B2

반응 노트

불러오는 중…