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

HRID 1613967노트

반응식

HRID 1613967 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9c04ea4c8fbc4048b91213d7c7ac5700
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05194602

반응 노트

불러오는 중…