Pyridine → 6-Methylergolin-8beta-ylmethyl tosylate
Reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][N:13]1[C@H:27]2[C@@H:17]([C:18]3[CH:19]=[CH:20][CH:21]=[C:22]4[C:28]=3[C:25]([CH2:26]2)=[CH:24][NH:23]4)[CH2:16][C@@H:15]([CH2:29][OH:30])[CH2:14]1.N1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)([O:30][CH2:29][C@@H:15]1[CH2:16][C@H:17]2[C@@H:27]([CH2:26][C:25]3[C:28]4[C:22](=[CH:21][CH:20]=[CH:19][C:18]2=4)[NH:23][CH:24]=3)[N:13]([CH3:12])[CH2:14]1)(=[O:9])=[O:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
5.0 g of p-toluenesulfonyl chloride was added in small portions to a mixture of 5.0 g of 6-methylergolin-8β-ylmethanol and 50 ml of pyridine while stirring, and the resulting mixture was stirred for 3 hours. After completion of the reaction, 4 ml of water was added to the mixture which was then stirred for 30 minutes. The mixture was diluted with ice-water, rendered alkaline with potassium carbonate and allowed to stand. The precipitated crystals were separated by filtration, washed with water and dried to obtain 6.9 g of the titled compound as colorless crystals. The crystals thus obtained were recrystallized from dichloromethane-isopropyl acetate to obtain colorless leaflets having a melting point of 195°-199° C. (with decomposition).
Workup
- stirringthe resulting mixture was stirred for 3 hours
- additionwas added to the mixture which
- stirringwas then stirred for 30 minutes
- customThe precipitated crystals were separated by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-c0374c64ae414f77a8d88caea36edc39
- Source dataset
- uspto-grants-1987_12
- Patent number
- US04713457
Reaction notes
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