Hydrochloric Acid → Levonorgestrel

HRID 1415022

Reaction equation

HRID 1415022 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH2:14][C:15](=[O:20])[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@:4]2([C:22]#[CH:23])[OH:21])[CH3:2].CO.Cl>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:22]#[CH:23])[OH:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 29979902Levonorgestrel EP Impurity B

Product 1

HCID 13109Levonorgestrel

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Stir 13β-ethyl-17α-ethynyl-17β-hydroxy-gon-5(10)-en-3-one (0.1 g.) with a mixture of methanol (36 cc.), water (1.6 cc.) and concentrated hydrochloric acid (2.4 cc.) for 1 hour. Add water and extract the mixture with ether. Wash, dry and evaporate the ethereal solution and recrystallize the residue from ether-hexane to obtain the title compound, m.p. 203°-6° undepressed on admixture with authentic material. Infrared spectrum 3.05, 3.5, 6.05, 9.4 μ.

Workup

  1. extractionAdd water and extract the mixture with ether
  2. washWash
  3. customdry
  4. customevaporate the ethereal solution
  5. customrecrystallize the residue from ether-hexane

Sources & evidence

ORD record
ord-42832c707e07449bb437a10f30a9d7d3
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Linked notes

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