Ethylenediamine → 3,3-Ethylenedioxy-17-(nitromethylene)androst-5-en-9alpha-ol

HRID 1613967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613967
[CH2:1]1[CH2:25][O:24][C:3]2([CH2:20][CH2:19][C@@:18]3([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]4[C@:17]3([OH:22])[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C:12]3=O)[CH2:4]2)[O:2]1.NCCN.[N+:30]([CH3:33])([O-:32])=[O:31]>>[CH2:1]1[CH2:25][O:24][C:3]2([CH2:20][CH2:19][C@@:18]3([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]4[C@:17]3([OH:22])[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C:12]3=[CH:33][N+:30]([O-:32])=[O:31])[CH2:4]2)[O:2]1

Komponenten

4

Edukt 3

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 151267113,3-Ethylenedioxy-9alpha-hydroxyandrost-5-en-17-one

Produkt 1

HCID 569874143,3-Ethylenedioxy-17-(nitromethylene)androst-5-en-9alpha-ol

Versuchsvorschrift

To a solution of 3,3-ethylenedioxy-9α-hydroxyandrost-5-en-17-one (3.46 g) in nitromethane (75 ml) under a nitrogen atmosphere 1,2-diaminoethane (0.1 ml) was added at reflux temperature. After 24 hours of refluxing the reaction was almost complete as measured by TLC. After cooling to room temperature the reaction mixture was concentrated under reduced pressure to give a solid, which was purified by column chromatography (silica gel; methylene chloride/diethyl ether 1/1) to provide the title compound.

Aufarbeitung

  1. temperatureat reflux temperature
  2. temperatureAfter 24 hours of refluxing the reaction
  3. concentrationwas concentrated under reduced pressure
  4. customto give a solid, which
  5. customwas purified by column chromatography (silica gel; methylene chloride/diethyl ether 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-9c04ea4c8fbc4048b91213d7c7ac5700
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194602

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