Potassium Hydroxide → 1-Cyclopentyl-6-methylergoline-8-carboxylic acid

HRID 570044Notes

Reaction equation

HRID 570044 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][C:16]=4[CH:6]2[CH2:5][CH:4]([C:18]([OH:20])=[O:19])[CH2:3]1)[NH:11][CH:10]=3.[OH-].[K+].C1(C)C=CC(S(O[CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)(=O)=O)=CC=1>CS(C)=O>[CH:33]1([N:11]2[C:12]3[C:17]4[C:9]([CH2:8][C@@H:7]5[C@@H:6]([C:16]=4[CH:15]=[CH:14][CH:13]=3)[CH2:5][CH:4]([C:18]([OH:20])=[O:19])[CH2:3][N:2]5[CH3:1])=[CH:10]2)[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 317685Cyclopentyl 4-methylbenzene-1-sulfonate2×HCID 622987NoName_3979

Product 1

HCID 572565691-Cyclopentyl-6-methylergoline-8-carboxylic acidYield 87.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 500 ml, three-neck round bottom flask was added 10.0 g (33.9 mmol) of 92% pure 9,10-dihydrolysergic acid, 11.72 g (180.0 mmol) of 86% pure powdered potassium hydroxide and 150 ml of DMSO. The mixture was stirred for 15 minutes and 10.22 g (42.6 mmol) of p-toluenesulfonic acid, cyclopentyl ester was added. The mixture was stirred at room temperature for about 20 hours and an additional 3.11 g (13.0 mmol) of p-toluenesulfonic acid, cyclopentyl ester was added. The mixture was stirred for an additional two hours and was poured into 750 ml of ice water. The mixture was washed twice with 200 ml portions of ethyl acetate and the pH of the aqueous phase was lowered to about 5 with glacial acetic acid. The mixture was cooled and the precipitated solid was collected by vacuum filtration. The solid was washed with water and dried under vacuum to provide 10.05 g of the title compound having a purity of 96.3 %. Yield 85.2%. Exact mass: theory 339.20725; found 339.20633.

Workup

  1. stirringThe mixture was stirred at room temperature for about 20 hours
  2. stirringThe mixture was stirred for an additional two hours
  3. washThe mixture was washed twice with 200 ml portions of ethyl acetate
  4. temperatureThe mixture was cooled
  5. filtrationthe precipitated solid was collected by vacuum filtration
  6. washThe solid was washed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f575fdb960b541dbb85960bef338f33e
Source dataset
uspto-grants-1988_03
Patent number
US04734501

Reaction notes

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