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Basic Information
CAS No.: 72821-79-5
Name: 6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID METHYL ESTER
Article Data: 6
Molecular Structure:
Molecular Structure of 72821-79-5 (6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID METHYL ESTER)
Formula: C19H22 N2 O2
Molecular Weight: 310.396
Synonyms: Ergoline-8-carboxylicacid, 6-(2-propenyl)-, methyl ester, (8b)- (9CI); Indolo[4,3-fg]quinoline,ergoline-8-carboxylic acid deriv.
Density: 1.19g/cm3
Boiling Point: 474.1°C at 760 mmHg
Flash Point: 240.5°C
PSA: 45.33000
LogP: 2.79500
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methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Conditions
ConditionsYield
With triethylamine at 20℃; Product distribution / selectivity;96.5%
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methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

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methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 35℃; for 2.5h;94%
With potassium carbonate In N,N-dimethyl-formamide80%
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methyl ergoline-8β-carboxylate hydrochloride

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allyl bromide

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methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Conditions
ConditionsYield
With triethylamine In N,N-dimethylformide at 20 - 30℃; for 4 - 5h; Product distribution / selectivity;
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methanol

81409-90-7

cabergoline

72821-79-5

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Conditions
ConditionsYield
With triethylamine
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9,10-dihydrolysergic acid methyl ester

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methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere
2: zinc / methanol; acetic acid / 1.08 h / 20 °C
3: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
View Scheme
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9-methyl 7-(2,2,2-trichloroethyl) (6aR,9R,10aR)-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxylate

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methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc / methanol; acetic acid / 1.08 h / 20 °C
2: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
View Scheme
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Dihydroergocryptine

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methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydroxide; sodium dithionite / water / 4 h / Reflux
2: sulfuric acid / 15 h / 20 °C
3: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere
4: zinc / methanol; acetic acid / 1.08 h / 20 °C
5: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
View Scheme
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9,10-dihydrolysergic acid

72821-79-5

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid / 15 h / 20 °C
2: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere
3: zinc / methanol; acetic acid / 1.08 h / 20 °C
4: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
View Scheme
72821-79-5

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

72821-88-6

[(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-yl]methanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 0.75h; Inert atmosphere; Cooling with ice;87%
With sodium tetrahydroborate
With sodium borohydrid In 1,4-dioxane; methanol
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methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

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1-amino-3-(dimethylamino)propane

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(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
In acetic acid Heating;85%
With 2-hydroxypyridin In ethylene glycol at 100℃; for 18h;85%
With acetic acid for 24h; Reflux;74%
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