Potassium hydride → Mesaconine

HRID 439570Notes

Reaction equation

HRID 439570 reaction equation
CC([O:4][C@:5]12[C@@H:33]3[CH:34]4[N:35]([CH3:37])[CH2:36][C@@:30]5([CH2:40][O:41][CH3:42])[C@@H:31]([C@H:32]3[O:38][CH3:39])[C@@:26]4([C@@H:27]([O:44][CH3:45])[CH2:28][C@H:29]5[OH:43])[C@@H:7]3[CH2:8][C@:9]([OH:25])([C@@H:20]([O:23][CH3:24])[C@@H:21]1[OH:22])[C@H:10]([O:11]C(C1C=CC=CC=1)=O)[C@H:6]23)=O.[H-].[K+]>CO>[CH3:37][N:35]1[C@H:34]2[C@:26]34[C@@H:7]5[CH2:8][C@:9]6([OH:25])[C@@H:20]([O:23][CH3:24])[C@H:21]([OH:22])[C@@:5]([OH:4])([C@H:6]5[C@H:10]6[OH:11])[C@H:33]2[C@H:32]([O:38][CH3:39])[C@@H:31]3[C@@:30]([CH2:40][O:41][CH3:42])([C@H:29]([OH:43])[CH2:28][C@@H:27]4[O:44][CH3:45])[CH2:36]1

Participants

4

Reactant 2

HCID 82127Potassium hydrideHCID 441747HCID 441747, compound

Product 1

HCID 101671037MesaconineYield 55.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mesaconitine 70 mg was dissolved in 5 ml of methanol. To this solution, 1 ml of 5% potassium hydride was added, and the mixture was heated under reflux for 3 hours. After methanol in the reaction mixture was distilled off, 5 ml of water was added to the residue and the mixture was extracted three times with 10 ml of methylene chloride. The extract was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The residue was subjected to thin-layer chromatography for separation and purification (eluting solvent: 10% methanol/ammonia-saturated chloroform) to give mesaconine (30 mg). 14-O-p-Chlorobenzoylmesaconine 20 mg was obtained in the same manner as in Example 90, except for the use of 30 mg of mesaconine and 30 mg of p-chlorobenzoyl chloride as each substitute for 30 mg of aconine and 30 mg of m-chlorobenzoyl chloride in Example 90.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. distillationAfter methanol in the reaction mixture was distilled off
  4. addition5 ml of water was added to the residue
  5. extractionthe mixture was extracted three times with 10 ml of methylene chloride
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue was subjected to thin-layer chromatography for separation and purification (eluting solvent: 10% methanol/ammonia-saturated chloroform)

Sources & evidence

ORD record
ord-7df37bb93b7d44858ff65233483dc1d5
Source dataset
uspto-grants-1996_05
Patent number
US05514684

Reaction notes

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