Levonorgestrel → 13beta-Ethyl-17alpha-vinyl-17beta-hydroxy-gon-4-en-3-one

HRID 1415021

Reaction equation

HRID 1415021 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([C:22]#[CH:23])[OH:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2].[H][H]>N1C=CC=CC=1.C(=O)([O-])[O-].[Ca+2].[Pd+2].C(=O)([O-])[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([CH:22]=[CH2:23])[OH:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

5

Reactant 2

HCID 13109LevonorgestrelHCID 178418361HCID 178418361, compound2×

Product 1

HCID 6814443013beta-Ethyl-17alpha-vinyl-17beta-hydroxy-gon-4-en-3-one

Reagents, catalysts & solvents 2

HCID 17803853Palladium on calcium carbonateCatalystHCID 1049PyridineSolvent

Procedure

Shake 13β-ethyl-17α-ethynyl-17β-hydroxy-gon-4-en-3-one (0.5 g.) in pyridine (20 cc.) containing a 2% palladium-calcium carbonate catalyst (150 mg.) with hydrogen at atmospheric pressure until one molecular equivalent of hydrogen has been absorbed. Recrystallise the product twice from ether-hexane and dry for 4 hours at 65°/0.005 mm. to yield the title compound, m.p. 108°-111°; ultraviolet absorption peak at 240 (ε15,200); infrared absorption peak at 10.9μ.

Workup

  1. customhas been absorbed
  2. customRecrystallise the product twice from ether-hexane
  3. customdry for 4 hours at 65°/0.005 mm

Sources & evidence

ORD record
ord-efc5131816b64e5cb88d68ab158b29f2
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Linked notes

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