Ammonia → Levonorgestrel

HRID 1729782Notes

Reaction equation

HRID 1729782 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2].N.[C-:23]#[C-:24].[K+].[K+]>CC(C)=O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@:4]2([C:23]#[CH:24])[OH:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 1037926413-Ethylgon-4-ene-3,17-dioneHCID 178462444HCID 178462444, compound

Product 1

HCID 13109Levonorgestrel

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

500 Mg. of 13β-ethyl-gon-4-en-3,17-dione produced in Example 135, was dissolved in 10 ml. of a benzene-ether solvent mixture (1:1) and added to a solution of 50 ml. of liquid ammonia containing 0.1 ml. of acetone and 0.5 g. of potassium acetylide. The reaction mixture was agitated at the ammonia boiling point for 2 hours and then the ammonia was evaporated at room temperature. The organic materials were extracted with ether and then the solvent was evaporated in vacuo. The residue was purified by chromatography over 50 g. of silica gel and on elution with a benzene-ethyl acetate mixture, afforded 13β-ethyl-17α-ethynyl-17-hydroxy-gon-4-en-3-one.

Workup

  1. customthe ammonia was evaporated at room temperature
  2. extractionThe organic materials were extracted with ether
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by chromatography over 50 g
  5. washof silica gel and on elution with a benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-8c8a3e6296bf4d65a28e2937f9b62ecd
Source dataset
uspto-grants-1976_11
Patent number
US03989724

Reaction notes

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