Potassium Carbonate → HCID 69448964, Verbindung

HRID 1593021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593021
[CH2:1]([CH:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]1=[O:9])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CS(O[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)(=O)=O>CN(C=O)C>[CH2:1]([CH:3]1[C:4](=[O:9])[N:5]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[C:6](=[O:8])[NH:7]1)[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2532172-EthylhydantoinHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Produkt 1

HCID 69448964HCID 69448964, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 5-ethylimidazoline-2,4-dione (1 g) in DMF (40 ml) was added potassium carbonate (2.16 g) followed by tert-butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (2.18 g) and the resulting mixture was heated to 100° C. for 18 hours. The reaction mixture was concentrated under reduced pressure and then was partitioned between dichloromethane and water. The organic layer was collected, dried and evaporated to dryness. The residue was purified by chromatography on silica eluting with a gradient of isohexane to ethyl acetate/isohexane (1:1) to give tert-butyl 4(4-ethyl-2,5-dioxoimidazolidin-1-yl)piperidine-1-carboxylate as a solid. Yield 1.12 g. NMR (CDCl3): 0.95 (t, 3H), 1.5 (s, 9H), 1.9 (m, 2H), 2.35 (m, 2H), 2.7 (m, 2H), 3.8-4.0 (m, 3H), 4.1 (q, 2H), 5.6 (bs, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customwas partitioned between dichloromethane and water
  3. customThe organic layer was collected
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography on silica eluting with a gradient of isohexane to ethyl acetate/isohexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-efe153da3f394f4e9f915650a34ede32
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294636B2

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