p-Toluenesulfonic acid → Ganaxolone

HRID 2253825Notes

Reaction equation

HRID 2253825 reaction equation
[OH:1][C@:2]1([CH3:27])[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12]2(OCC[O:14]2)[CH3:13])[CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[OH:1][C@:2]1([CH3:27])[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 695675983alpha-Hydroxy-3beta-methyl-20,20-ethylenedioxy-5alpha-pregnane

Product 1

HCID 6918305Ganaxolone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3α-hydroxy-3β-methyl-20,20-ethylenedioxy-5α-pregnane and p-toluene sulfonic acid (catalytic) in wet acetone was heated at reflux overnight. The reaction was concentrated in vacuo and taken up in chloroform. The organic phase was washed with sodium bicarbonate, dried over magnesium sulfate, concentrated, and recrystallized from methanol to give the titled compound.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction was concentrated in vacuo
  3. washThe organic phase was washed with sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-3d6e5685c5db415e898194c201cf290a
Source dataset
uspto-grants-1993_08
Patent number
US05232917

Reaction notes

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