Ammonia → Ergoline-8-methanol, 2-bromo-9,10-didehydro-6-methyl-, (8beta)-
Reaction equation
[BrH:1].[OH-].[Na+].[OH:4][CH2:5][C@@H:6]1[CH:21]=[C:20]2[C@@H:10]([CH2:11][C:12]3[C:22]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]2=4)[NH:14][CH:13]=3)[N:8]([CH3:9])[CH2:7]1.N>Br.CS(C)=O.CS(C)=O>[Br:1][C:13]1[NH:14][C:15]2[C:22]3[C:12]=1[CH2:11][C@@H:10]1[C:20]([C:19]=3[CH:18]=[CH:17][CH:16]=2)=[CH:21][C@@H:6]([CH2:5][OH:4])[CH2:7][N:8]1[CH3:9]Participants
Procedure
Dry gaseous hydrogen bromide is introduced into 100 ml of anhydrous dimethylsulfoxide at room temperature. The quantity of the introduced hydrogen bromide gas is measured by titrating with 0.1N sodium hydroxide solution. The hydrogen bromide is introduced until the concentration of the gas reaches 0.0003-0.0005 mole/ml. One g (0.003937 mole) of lysergol is dissolved in an aliquot amount of this hydrogen bromide-dimethylsulfoxide mixture which contains 12 equivalents of hydrogen bromide. After complete dissolution, this mixture is stirred at room temperature for 20 minutes, then poured into a 5-fold volume of ice-water. Thereafter, the solution is made alkaline by adding aqueous ammonia up to a pH value of 8.9, the precipitate is filtered off, washed with water, dried and purified on a Kieselgel column by using an 8:2 mixture of chloroform and methanol to give the named compound in a yield of 0.76 g (0.00228 mole, 58%), m.p.: 193° C.
Workup
- dissolutionAfter complete dissolution
- filtrationthe precipitate is filtered off
- washwashed with water
- customdried
- custompurified on a Kieselgel column
- additionan 8:2 mixture of chloroform and methanol
- customto give the named compound in a yield of 0.76 g (0.00228 mole, 58%), m.p.: 193° C.
Sources & evidence
- ORD record
- ord-7c40ca1910e946b4ba0b0e83acfaf28b
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04859682
Reaction notes
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