2-Pyrrolidone → Levcromakalim

HRID 1905780

Reaktionsgleichung

Reaktionsgleichung von HRID 1905780
C(C1C=CC2OC(C)(C)[C@@H](Br)[C@H](O)C=2C=1)#N.[H-].[Na+].[C:19]([C:21]1[CH:33]=[CH:32][C:24]2[O:25][C:26]([CH3:31])([CH3:30])[CH:27]3[O:29][CH:28]3[C:23]=2[CH:22]=1)#[N:20].[NH:34]1[CH2:38][CH2:37][CH2:36][C:35]1=[O:39]>CS(C)=O.O>[C:19]([C:21]1[CH:33]=[CH:32][C:24]2[O:25][C:26]([CH3:31])([CH3:30])[C@@H:27]([OH:29])[C@H:28]([N:34]3[CH2:38][CH2:37][CH2:36][C:35]3=[O:39])[C:23]=2[CH:22]=1)#[N:20]

Komponenten

7

Edukt 4

HCID 120252-PyrrolidoneHCID 24758Sodium hydride2×HCID 6932483trans-2,2-Dimethyl-3-bromo-6-cyanochroman-4-olHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Produkt 1

HCID 93504LevcromakalimAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-bromo-4-hydroxy-2H-benzo[b]pyran (4 g, 14.2 mM) in dimethylsulphoxide (20 ml) was stirred and sodium hydride (60% dispersion in oil, 0.6 g, 15 mM) added. The suspension was stirred for 1 hour when a solution of 6-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran resulted. 2-Pyrrolidone (1.8 g, 21 mM) and further sodium hydride (0.8 g, 21 mM) were introduced and the mixture stirred at room temperature for an additional 16 hours. Water (40 ml) was slowly added to the mixture to induce crystallisation of the product after which it was cooled in ice and filtered under suction. Crystallisation from ethanol (20 ml) gave the title compound as a cream coloured solid in 60% yield. Recrystallisation from ethyl acetate afforded the pure product as needles, m.p. 226.5°-227.5° having an nmr spectrum and t.l.c. characteristics identical to those of the compound of Description 6.

Aufarbeitung

  1. customresulted
  2. customcrystallisation of the product after which it
  3. temperaturewas cooled in ice
  4. filtrationfiltered under suction
  5. customCrystallisation from ethanol (20 ml)

Quellen und Nachweise

ORD-Eintrag
ord-7280985195ea4d38820d82e3627e7466
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04647670

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