ChemicalBook CAS DataBase List Cabergoline

Cabergoline synthesis

10synthesis methods

Product Name:Cabergoline
CAS Number:81409-90-7
Molecular formula:C26H37N5O2
Molecular Weight:451.6

Cabergoline is an ergot derivative and a dopamine D2-receptor agonist. It inhibits the secretion of prolactin and growth hormone. Cardigerine can be synthesized from the reaction of 6-(2-propenyl) ergotrin-8 β -carboxylic acid (ⅰ) with carbonized diimine in tetrahydrofuran.

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591-87-7 Synthesis

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Yield:81409-90-7 92.3%

Reaction Conditions:

tetrakis(triphenylphosphine) palladium⁽⁰⁾ in toluene at 20; for 2 h;

Steps:

5

EXAMPLE 5; Synthesis of 6-allyl-N-[3-(dimethylamino)propyl]-N-[(ethylamino)carbonyl]-ergoline-8?- carboxamide (Cabergoline).; To a suspension of 9.0 g (21.87 mmol) N- [3- (dimethylamino) propyl] -N- [(ethylamino)carbonyl)-ergoline-8?-carboxamide (XIX) in 250 ml of toluene 0.5 g of tetrakis (triphenylphosphine) palladium (0) and 5 ml of allyl acetate was added, and the reaction mixture was stirred at ambient temperature for 2 hours. The resulting mixture was washed with 100 ml of water. The organic layer was dried over anhydrous sodium sulphate. The dried solution was concentrated in vacuum and the product was purified on a silica plug to give 9.1 g (92.3%) of the title compound. 1H NMR (DMSO-d6, TMS, 500MHz) 8 1.10 (t, 3H, J=7. 2Hz, CONHCH2CH3) ; 1.47 (q, 1H, J=12. 4Hz, Hp-9) ; 1.62-1. 72 (m, 2H, CONCH2CH2CH2N (CH3) 2) ; 2.15 (s, 6H, CONCH2CH2CH2N (CH3) 2); 2.20-2. 30 (m, 2H, CONHCH2CH2CH2N (CH3) 2); 2.32-2. 40 (m, 2H, H-5, Hp-7) ; 2.54 (dd, 1H, J=14. 3Hz, 11.2Hz, Hα-4) ; 2.68-2. 84 (m, 2H, Ha-9, H-10); 3.08 (ddd, 1H, J=11. 3Hz, 3. 1Hz, 1. 8Hz, Ha-7) ; 3.14-3. 22 (m, 2H, CONHCH2CH3) ; 3.26 (dd, 1H, J=14. 7Hz, 7.3Hz, HX-N (6) CH2CH=CH2) ; 3.28-3. 38 (m, 2H, Hp-4, H-8) ; 3.48 (dd, 1H, J=14. 7Hz, 5.8Hz, Hy-N (6) CH2CH=CH2) ; 3.58-3. 68 (m, 2H, CONCH2CH2CH2N (CH3) 2); 5.15 (d, 1H, J=10. 3Hz, HX-N (6) CH2CH=CH2) ; 5.24 (d, 1H, J=17. 2Hz, Hy-N (6) CH2CH=CH2) ; 5. 88-5. 98 (m, 1H, N (6) CH2CH=CH2) ; 6.75 (d, 1H, J=7. 0Hz, H-12); 6.97 (s, 1H, H-2); 7.01 (t, 1H, J=7. 5Hz, H-13); 7.13 (d, 1H, J=8. 0Hz, H-14) ; 9.04 (t, 1H, J=5. 0Hz, CONHCH2CH3) ; 10.60 (s, 1H, N (1) H).

References:

WO2005/85243,2005,A2 Location in patent:Page/Page column 22

85329-86-8 Synthesis