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

HRID 64706

Reaction equation

HRID 64706 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-21598c1f3df748a9a17a46da1a1ea233
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Linked notes

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