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Ethyl isocyanate → Cabergoline

HRID 1795467
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1795467
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[CH3:13][N:14]([CH3:40])[CH2:15][CH2:16][CH2:17][NH:18][C:19]([C@@H:21]1[CH2:35][C@H:34]2[C@@H:24]([CH2:25][C:26]3[C:36]4[C:29](=[CH:30][CH:31]=[CH:32][C:33]2=4)[NH:28][CH:27]=3)[N:23]([CH2:37][CH:38]=[CH2:39])[CH2:22]1)=[O:20].C(N(CC)CC)C.[CH2:48]([N:50]=[C:51]=[O:52])[CH3:49].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>ClCCl>[CH3:49][CH2:48][NH:50][C:51]([N:18]([C:19]([C@H:21]1[CH2:22][N:23]([CH2:37][CH:38]=[CH2:39])[C@H:24]2[C@@H:34]([C:33]3[C:36]4[C:26]([CH2:25]2)=[CH:27][NH:28][C:29]=4[CH:30]=[CH:31][CH:32]=3)[CH2:35]1)=[O:20])[CH2:17][CH2:16][CH2:15][N:14]([CH3:13])[CH3:40])=[O:52]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 2724141Tetrabutylammonium FluorideHCID 10927015N-(3-(Dimethylamino)propyl)-6-(2-propenyl)-ergoline-8-carboxamide, (8beta)-

Produkt 1

HCID 54746CabergolineAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
18 °C

Versuchsvorschrift

Trimethylsilyl trifluromethanesulfonate (7.6 g, 34.2 mmol, 1.1 eq) was added dropwise during 2 hours to a stirred mixture of N-[3-(dimethylamino)propyl]-6-allylergoline-8β-carboxamide (11.9 g, 31.5 mmol, 1 eq), triethylamine (3.8 g, 37.6 mmol, 1.2 eq) and dichloromethane (280 g) at −2° C. The mixture was stirred for 14 hours at 18° C. Ethyl isocyanate (11.1 g, 156.2 mmol, 5 eq) was added in one portion to the stirred mixture at 18° C. The obtained mixture was stirred for 48 hours at the same temperature. Tetrabutylammonium fluoride, 1.0 M solution in THF (30.4 g, 34.2 mmol, 1.1 eq) was added dropwise during 2 hours to the stirred mixture at −2° C. The reaction mixture was stirred for 2 hours at the same temperature and evaporated under reduced pressure. A solution of the residue in tert-butyl methyl ether was washed with aqueous solution of sodium bicarbonate and aqueous solution of sodium chloride, dried over sodium sulfate and passed through short silica gel column. The column was washed with acetone and the acetone solution was evaporated under reduced pressure to give 9.6 g (68.2%) of cabergoline as amorphous solid with 98% purity by HPLC. A hot solution of the amorphous cabergoline in tert-butyl methyl ether was kept at 0–5° C. for 60 hours. The precipitated solid was filtered off, washed on the filter with cold tert-butyl methyl ether and dried under reduced pressure at 15–25° C. to give 8.5 g (50%) solvate form A of cabergoline as white crystals with mp 66–70° C. and 99.8% purity by HPLC.

Aufarbeitung

  1. stirringThe obtained mixture was stirred for 48 hours at the same temperature
  2. stirringThe reaction mixture was stirred for 2 hours at the same temperature
  3. customevaporated under reduced pressure
  4. washA solution of the residue in tert-butyl methyl ether was washed with aqueous solution of sodium bicarbonate and aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. washThe column was washed with acetone
  7. customthe acetone solution was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7239153e537c4ac3988119579643c739
Quelldatensatz
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07026483B2

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