N,N-Dimethylaniline → 16beta-Ethyl-17beta-(2-bromo-2-methylpropionyloxy)4-estren-3-one

HRID 64706

반응식

HRID 64706 반응식
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[OH:22])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].CN(C)C1C=CC=CC=1.[Br:32][C:33]([CH3:38])([CH3:37])[C:34](Br)=[O:35].C(OCC)(=O)C>ClCCl>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:34](=[O:35])[C:33]([Br:32])([CH3:38])[CH3:37])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

참가 물질

6

반응물 4

HCID 949N,N-DimethylanilineHCID 8857Ethyl AcetateHCID 886852-Bromo-2-methylpropionyl bromideHCID 443947Oxendolone

생성물 1

HCID 7046730516beta-Ethyl-17beta-(2-bromo-2-methylpropionyloxy)4-estren-3-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In 30 ml of dichloromethane are dissolved 3.2 g of 16β-ethyl-17β-hydroxy-4-estren-3-one and 1.2 ml of dimethylaniline and, with stirring at room temperature (15°-25° C.), 1.0 ml of 2-bromo-2-methylpropionyl bromide is added to the above solution. The mixture is stirred at room temperature (15°-25° C.) for 16 hours, followed by addition of 300 ml of ethyl acetate. The mixture is washed with 10% phosphoric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in that order and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 400 ml of diisopropyl ether-n-hexane (1:1), elution is carried out with 800 ml of the same solvent system. The eluate is evaporated under reduced pressure to remove the solvent, giving 2.6 g of the above-identified compound as a light-yellow viscous oil.

후처리

  1. additionis added to the above solution
  2. washThe mixture is washed with 10% phosphoric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is then distilled off under reduced pressure
  5. washpassage of 400 ml of diisopropyl ether-n-hexane (1:1), elution
  6. customThe eluate is evaporated under reduced pressure
  7. customto remove the solvent

출처 및 근거

ORD 기록
ord-21598c1f3df748a9a17a46da1a1ea233
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609650

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