Sodium hydride → 1-(6-Methylergolin-8beta-ylmethyl)-2-propylimidazole
Reaction equation
[H-].[Na+].[CH2:3]([C:6]1[NH:7][CH:8]=[CH:9][N:10]=1)[CH2:4][CH3:5].S(C1C=CC(C)=CC=1)(O[CH2:15][C@@H:16]1[CH2:30][C@H:29]2[C@@H:19]([CH2:20][C:21]3[C:31]4[C:24](=[CH:25][CH:26]=[CH:27][C:28]2=4)[NH:23][CH:22]=3)[N:18]([CH3:32])[CH2:17]1)(=O)=O>CN(C)C=O>[CH3:32][N:18]1[C@H:19]2[C@@H:29]([C:28]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:31]=3[C:21]([CH2:20]2)=[CH:22][NH:23]4)[CH2:30][C@@H:16]([CH2:15][N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH2:3][CH2:4][CH3:5])[CH2:17]1Participants
5
Procedure
0.68 g of 50% sodium hydride in an oil was added in small portions to a mixture of 2.1 g of 2-propylimidazole and 50 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 2.5 hours. The solvent was distilled off under reduced pressure, and the residue was purified by alumina column chromatography (eluted with ethyl acetate:benzene=1:2, and then with ethyl acetate). The resulting product was recrystallized from acetone-hexane to obtain 0.8 g of the titled compound as colorless needles having a melting point of 223°-227° C. (with decomposition).
Workup
- temperaturewas then heated on a water bath for 2.5 hours
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by alumina column chromatography (
- washeluted with ethyl acetate
- customThe resulting product was recrystallized from acetone-hexane
Sources & evidence
- ORD record
- ord-ceed7b3ae9ae4f538ce56030095425d8
- Source dataset
- uspto-grants-1987_12
- Patent number
- US04713457
Reaction notes
Loading…