Sodium hydride → 3-(6-Methylergolin-8beta-ylmethyl)oxazolidin-2-one

HRID 986524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986524
[H-].[Na+].[O:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].S(C1C=CC(C)=CC=1)(O[CH2:13][C@@H:14]1[CH2:28][C@H:27]2[C@@H:17]([CH2:18][C:19]3[C:29]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]2=4)[NH:21][CH:20]=3)[N:16]([CH3:30])[CH2:15]1)(=O)=O>CN(C)C=O>[CH3:30][N:16]1[C@H:17]2[C@@H:27]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:29]=3[C:19]([CH2:18]2)=[CH:20][NH:21]4)[CH2:28][C@@H:14]([CH2:13][N:5]2[CH2:6][CH2:7][O:3][C:4]2=[O:8])[CH2:15]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Produkt 1

HCID 103816823-(6-Methylergolin-8beta-ylmethyl)oxazolidin-2-oneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.5 g of 50% sodium hydride in an oil was added in small portions to a mixture of 2.0 g of oxazolidin-2-one and 15 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 1 hour. The solvent was distilled off under reduced pressure, and the residue (which was dissolved in dichloromethane and adsorbed on silica gel) was purified by silica gel column chromatography (eluted with ethyl acetate:isopropyl alcohol=1:1 by volume). The product was recrystallized from isopropyl alcohol to obtain 1.3 g of the titled compound as colorless needles having a melting point higher than 240° C. (with decomposition).

Aufarbeitung

  1. temperaturewas then heated on a water bath for 1 hour
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue (which was dissolved in dichloromethane and adsorbed on silica gel)
  4. customwas purified by silica gel column chromatography (eluted with ethyl acetate:isopropyl alcohol=1:1 by volume)
  5. customThe product was recrystallized from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-276f94bc1eb249d1bad7c1877b5ab976
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04713457

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