Trifluoroacetic acid → HCID 14107810, compound
Reaction equation
[CH2:1]([N:4]1[C@H:18]2[C@@H:8]([C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:19]=3[C:16]([CH2:17]2)=[CH:15][NH:14]4)[CH2:7][CH2:6][CH2:5]1)[CH2:2][CH3:3].[C:20](O)(C(F)(F)F)=O.C([SiH](CC)CC)C>>[CH3:20][C@@H:6]1[CH:7]=[C:8]2[C@@H:18]([CH2:17][C@H:16]3[C:19]4[C:13](=[CH:12][CH:11]=[CH:10][C:9]2=4)[NH:14][CH2:15]3)[N:4]([CH2:1][CH2:2][CH3:3])[CH2:5]1Participants
Procedure
A mixture of 1.5 g (6.7 mmol) of 6-desmethyllysergine (prepared by the N-demethylation of lysergine by cyanogen bromide), 1.8 g (13 mmol) of anhydrous potassium carbonate, 2.2 g (13 mmol) of 1-iodopropane and 50 ml of dry dimethylformamide was stirred for 42 hours. The solvent was evaporated in vacuo and the residue was digested with two 75 ml portions of ether and then filtered. The ether extracts were evaporated and the resulting solid residue was suspended in cold ether and collected by filtration to give 0.72 g (40%) of single spot material by thin layer chromatography (methanol:chloroform, 1:9). The NMR of the material was consistent with that expected for 6-propylergoline. Reduction was accomplished as described previously by stirring a mixture of 5 ml TFA, 1.3 g (11.1 mmol) of triethylsilane and 0.72 g (2.7 mmol) of 6-propyllysergine for 6 hours. The resultant was worked up as described above and gave 0.05 g of the title compound (7%) following HPLC and recrystallization from methanol/petane, mp. 135°-137° C.
Sources & evidence
- ORD record
- ord-d5e2bb4625804158bb5c4998e64bd8e6
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04798834
Reaction notes
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