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

HRID 64724Notes

Reaction equation

HRID 64724 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[O:22][C:23](=[O:26])[CH2:24][OH:25])[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.[CH3:36][CH:37]([CH2:41][CH2:42][CH3:43])[C:38](Cl)=[O:39]>ClCCl.C(OCC)(=O)C>[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:23](=[O:26])[CH2:24][O:25][C:38](=[O:39])[CH:37]([CH3:36])[CH2:41][CH2:42][CH3:43])[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 3

HCID 949N,N-DimethylanilineHCID 1073852-Methylvaleryl chlorideHCID 7046644116beta-Ethyl-17beta-glycoloyloxy-4-estren-3-one

Product 1

HCID 7046693016beta-Ethyl-17beta-(2-methylvaleryl)oxyacetoxy-4-estren-3-oneYield 19.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 20 ml of dichloromethane are dissolved 0.5 g of 16β-ethyl-17β-glycoloyloxy-4-estren-3-one and 0.2 ml of N,N-dimethylaniline, and 0.5 g of 2-methylvaleryl chloride is added to the above solution. The mixture is refluxed for 6 hours. After cooling, the reaction mixture is diluted with 150 ml of ethyl acetate 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 200 ml of diisopropyl ether-n-hexane (2:8), elution is carried out with 500 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.126 g of the above-identified compound as a light-yellow viscous oil.

Workup

  1. additionis added to the above solution
  2. temperatureThe mixture is refluxed for 6 hours
  3. temperatureAfter cooling
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent is then distilled off under reduced pressure
  6. washpassage of 200 ml of diisopropyl ether-n-hexane (2:8), elution
  7. additionis carried out with 500 ml of a 1:1 mixture of the same solvents
  8. customThe eluate is evaporated under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-6c373de8ad0a482ca08749a90e9f07a1
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Reaction notes

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