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

HRID 1613967Notes

Reaction equation

HRID 1613967 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9c04ea4c8fbc4048b91213d7c7ac5700
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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