Acetic Acid → Desogestrel

HRID 1446149

Reaction equation

HRID 1446149 reaction equation
[CH2:1]([C@:3]12[CH2:11][C:10](=[CH2:12])[C@@H:9]3[C@@H:13]4[C:18]([CH2:19][CH2:20][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][CH2:4]2)=[CH:17][CH2:16][CH2:15][CH2:14]4)[CH3:2].[C-]#[C-].[Li+].[Li+].[CH2:25](N)[CH2:26]N.C(O)(=[O:31])C>CS(C)=O.O>[CH3:2][CH2:1][C@@:3]12[C@:4]([OH:31])([C:25]#[CH:26])[CH2:5][CH2:6][C@H:7]1[C@@H:8]1[CH2:20][CH2:19][C:18]3[C@@H:13]([C@H:9]1[C:10](=[CH2:12])[CH2:11]2)[CH2:14][CH2:15][CH2:16][CH:17]=3

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3301EthylenediamineHCID 86601160HCID 86601160, compound2×HCID 178462446HCID 178462446, compound

Product 1

HCID 40973DesogestrelYield 89%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

100 g (0.35 moles) of 13-ethyl-11-methylen-gon-4-ene (compound XVIII) were dissolved in anhydrous dimethylsulfoxide (3 liters) under stirring at room temperature. 430 g of lithium acetylide complexed with ethylendiamine were added to the so obtained solution and the stirring at room temperature was carried on for 21 hours. After this period the reaction was spilled in water cooled at a temperature of 2° C. (3 liters) then a 10% aqueous solution of acetic acid was added (7 liters) and the aqueous phase was extracted with dichloromethane (3×2 liters). The organic extracts were subsequently washed with a saturated solution of sodium bicarbonate (2 liters) and then with a saturated solution of sodium chloride. The organic phase was then dehydrated on sodium sulfate, filtered and evaporated to dryness to give 96.24 g (0.31 moles; yields 89%) of Desogestrel.

Workup

  1. additionwere added to the so obtained solution
  2. customstirring at room temperature
  3. customwas carried on for 21 hours
  4. temperaturecooled at a temperature of 2° C. (3 liters)
  5. extractionthe aqueous phase was extracted with dichloromethane (3×2 liters)
  6. washThe organic extracts were subsequently washed with a saturated solution of sodium bicarbonate (2 liters)
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-e0d36b3652984a508820e022f412fb9d
Source dataset
uspto-grants-2010_02
Patent number
US07667056B2

Linked notes

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