반응 #320819

ord-baca649f45d847738a6a8a062ada55cc

반응 방정식

CCOC(=O)N=NC(=O)OCC
diethyl azodicarboxylate
C[C@]12CC[C@H](OCCO)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccoc3)CC[C@]12O
3β-(2-hydroxyethoxy)-17β-(3-furyl)-5β-androstan-14β-ol
O=C1NC(=O)c2ccccc21
phthalimide
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
→
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
수율 70.7%

반응물

CCOC(=O)N=NC(=O)OCC
diethyl azodicarboxylate
C[C@]12CC[C@H](OCCO)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccoc3)CC[C@]12O
3β-(2-hydroxyethoxy)-17β-(3-furyl)-5β-androstan-14β-ol
O=C1NC(=O)c2ccccc21
phthalimide
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine

시약

없음

용매

C1CCOC1
tetrahydrofuran

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타After 2 hrs the solvent was removed in vacuo
  2. 2
    건조the crude product was dried over anhydrous sodium sulfate
  3. 3
    기타evaporated to dryness under reduced pressure
  4. 4
    기타The crude product was purified by flash-chromatography (SiO2)

실험 절차

A solution of 0.29 ml of diethyl azodicarboxylate was added dropwise, under nitrogen, to a solution of 0.75 g of 3β-(2-hydroxyethoxy)-17β-(3-furyl)-5β-androstan-14β-ol, 0.28 g of phthalimide and 0.50 g of triphenylphosphine in 7 ml of tetrahydrofuran at room temperature. After 2 hrs the solvent was removed in vacuo, the crude product was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 80/20 to give 0.70 g of 3β-(2-phthalimidoethoxy)-17β-(3-furyl)-5β-androstan-14β-ol.

출처

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