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

HRID 1613967ノート

反応式

HRID 1613967 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9c04ea4c8fbc4048b91213d7c7ac5700
出典データセット
uspto-grants-1993_03
特許番号
US05194602

反応ノート

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