Potassium Hydroxide → 1-(1-Ethylpropyl)-6-methylergoline-8carboxylic acid

HRID 570043Notes

Reaction equation

HRID 570043 reaction equation
[OH-].[K+].[CH3:3][N:4]1[CH:9]2[CH2:10][C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][C:18]=4[CH:8]2[CH2:7][CH:6]([C:20]([OH:22])=[O:21])[CH2:5]1)[NH:13][CH:12]=3.[C:23]1(C)[CH:28]=[CH:27]C(S(OC(CC)CC)(=O)=O)=[CH:25][CH:24]=1>CS(C)=O>[CH2:24]([CH:23]([N:13]1[C:14]2[C:19]3[C:11]([CH2:10][C@@H:9]4[C@@H:8]([C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH2:7][CH:6]([C:20]([OH:22])=[O:21])[CH2:5][N:4]4[CH3:3])=[CH:12]1)[CH2:28][CH3:27])[CH3:25]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 622987NoName_3979HCID 12568537Pentan-3-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 138780051-(1-Ethylpropyl)-6-methylergoline-8carboxylic acidYield 68.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 500 ml, three-neck round bottom flask was charged with 11.72 g (180.0 mmol) of 86% pure powdered potassium hydroxide, 10.0 g (33.9 mmol) of 92% pure 9,10-dihydrolysergic acid and 150 ml of DMSO. The mixture was stirred at room temperature for 15 minutes, and 10.3 g (42.6 mmol) of p-toluenesulfonic acid, 1-ethylpropyl ester was added. The mixture was stirred at room temperature for 19 hours, and 1000 ml of ice water was added. The mixture was washed twice with 250 ml aliquots of ethyl acetate, and the pH of the aqueous layer was adjusted to 5 with glacial acetic acid. The mixture was cooled and the precipitated solid was collected by vacuum filtration. The solid was dried under vacuum to provide 7.94 g of 1-(1-ethylpropyl)-6-methylergoline-8carboxylic acid. A second crop of material was obtained to provide 0.9 g of product. The purity of the first crop was 96.7%, and the purity of the second crop was 96%. Total yield 72.1%. The identity of the product was determined by thin layer chromatography as compared to an authentic reference standard.

Workup

  1. stirringThe mixture was stirred at room temperature for 19 hours
  2. washThe mixture was washed twice with 250 ml aliquots of ethyl acetate
  3. temperatureThe mixture was cooled
  4. filtrationthe precipitated solid was collected by vacuum filtration
  5. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-2c9731d0103b4e419fe8e58e1944b35b
Source dataset
uspto-grants-1988_03
Patent number
US04734501

Reaction notes

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