Pyrrolidine → 8-(1-hydroxyethyl)-2-morpholino-6-(pyrrolidine-1-carbonyl)-4H-chromen-4-one

HRID 572786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572786
[B-](F)(F)(F)F.CN(C(O[N:14]1[C:19](=O)[CH2:18][CH2:17][C:15]1=O)=[N+](C)C)C.[OH:21][CH:22]([C:24]1[CH:25]=[C:26]([C:41](O)=[O:42])[CH:27]=[C:28]2[C:33]=1[O:32][C:31]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[CH:30][C:29]2=[O:40])[CH3:23].C(N(C(C)C)C(C)C)C.N1CCCC1>C(Cl)Cl>[OH:21][CH:22]([C:24]1[CH:25]=[C:26]([C:41]([N:14]2[CH2:15][CH2:17][CH2:18][CH2:19]2)=[O:42])[CH:27]=[C:28]2[C:33]=1[O:32][C:31]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[CH:30][C:29]2=[O:40])[CH3:23]

Komponenten

6

Edukt 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 582349808-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

Produkt 1

HCID 582350218-(1-hydroxyethyl)-2-morpholino-6-(pyrrolidine-1-carbonyl)-4H-chromen-4-oneAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2-(2,5-dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (3.34 g, 11.09 mmol) at 25° C. was added portionwise to 8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (1.77 g, 5.54 mmol) and N-ethyl-N-isopropylpropan-2-amine (2.028 mL, 11.64 mmol) suspended in DCM (15 mL) under nitrogen. The resulting mixture was stirred at 25° C. for 5 hrs. Pyrrolidine (1.388 mL, 16.63 mmol) was then added to the mixture and the resulting mixture was stirred at 25° C. overnight. The mixture was poured onto a silica gel column and purified by flash chromatography eluting with 2 to 7% methanolic ammonia (7 N) in DCM. The solvent was evaporated to dryness, the residue was triturated in ethylacetate (10 mL), collected by filtration and dried to afford 8-(1-hydroxyethyl)-2-morpholino-6-(pyrrolidine-1-carbonyl)-4H-chromen-4-one (1.66 g, 80%) as a beige solid. Mass Spectrum: M+H+ 373.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 25° C. overnight
  2. additionThe mixture was poured onto a silica gel column
  3. custompurified by flash chromatography
  4. washeluting with 2 to 7% methanolic ammonia (7 N) in DCM
  5. customThe solvent was evaporated to dryness
  6. customthe residue was triturated in ethylacetate (10 mL)
  7. filtrationcollected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b66787a6d6dd4528972d2dd71474a7c7
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029374B2

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