반응 #320820

ord-0e04e411c2934cb38e63c3a96fceec3c

반응 방정식

O
water
C[C@]12CC[C@H](OCCN3C(=O)c4ccccc4C3=O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccoc3)CC[C@]12O
3β-(2-phthalimidoethoxy)-17β-(3-furyl)-5β-androstan-14β-ol
NN.O
hydrazine hydrate
→
C[C@]12CC[C@H](OCCN)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccoc3)CC[C@]12O
title compound
수율 92.7%
C[C@]12CC[C@H](OCCN)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccoc3)CC[C@]12O
3β-(2-Aminoethoxy)-17β-(3-furyl)-5β-androstan-14β-ol
수율 92.7%

반응물

O
water
C[C@]12CC[C@H](OCCN3C(=O)c4ccccc4C3=O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccoc3)CC[C@]12O
3β-(2-phthalimidoethoxy)-17β-(3-furyl)-5β-androstan-14β-ol
NN.O
hydrazine hydrate

시약

없음

용매

CCO
ethanol

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도at reflux for 4 hrs
  2. 2
    workup.DISTILLATIONthe ethanol distilled under reduced pressure
  3. 3
    추출The residue was extracted with methylene chloride
  4. 4
    세척the organic solution was washed with water
  5. 5
    건조dried over anhydrous sodium sulfate
  6. 6
    기타evaporated to dryness under reduced pressure
  7. 7
    기타The crude residue was purified by flash-chromatography (SiO2)

실험 절차

To a solution of 0.50 g of 3β-(2-phthalimidoethoxy)-17β-(3-furyl)-5β-androstan-14β-ol in 50 ml of ethanol (96%) 0.19 g of hydrazine hydrate were added at room temperature. The mixture was kept at reflux for 4 hrs, then 10 ml of water were added and the ethanol distilled under reduced pressure. The residue was extracted with methylene chloride, the organic solution was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude residue was purified by flash-chromatography (SiO2) using methylene chloride/methanol 90/10 as eluant to give 0.35 g of the title compound (I-aa) as a white solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05593982uspto-grants-1997_01