ChemicalBook CAS DataBase List 6-Allyl-8beta-carboxyergoline

6-Allyl-8beta-carboxyergoline synthesis

7synthesis methods

Product Name:6-Allyl-8beta-carboxyergoline
CAS Number:81409-74-7
Molecular formula:C18H20N2O2
Molecular Weight:296.36

6-(2-PROPENYL)-ERGOLINE-8-CARBOXYLIC ACID METHYL ESTER

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Yield: 85%

Reaction Conditions:

Stage #1:methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate with sodium hydroxide;water in methanol at 20 - 30; for 2 - 3 h;
Stage #2: with hydrogenchloride in methanol;water; pH=6 - 6.5 at 0 - 5; for 1 - 2 h;

Steps:

10
To a mixture of methyl ergoline-8μ-carboxylate hydrochloride (185 g) and triethylamine (183.3 g) in N,N-dimethylformide (555 mL) is added allyl bromide (146.3 g). The mixture is stirred at 20-30° C. for 4-5 h or until the reaction completion. The reaction mixture is then cooled to 0-5° C. and to it is added water (1.3 L) in portions. The resulting suspension is stirred at 0-5° C. for 1-3 h, then is filtered and washed with N,N-dimethylformide/water (1:2 v/v) and then water to give methyl 6-(2-propenyl)-ergoline-8β-carboxylate.The damp product is mixed with methanol (925 mL) and to it is added 50% sodium hydroxide solution (63 g). After stirring at 20-30° C. for 2-3 h, water (500 mL) is added and the pH of the mixture is adjusted to 6-6.5 by the slow addition of hydrochloric acid. The resulting suspension is stirred at 0-5° C. for 1-2 h, then filtered, washed with water and methanol. The isolated solid is dried to give 6-(2-propenyl)-ergoline-8β-carboxylic acid (152.3 g) in 85% yield.

References:

Apotex Pharmachem Inc. US2008/275240, 2008, A1 Location in patent:Page/Page column 11-12