Potassium tert-butoxide → HCID 86680441, Verbindung

HRID 1184579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184579
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]1[C:19]([O:21]C)=O.CC(C)([O-])C.[K+]>O1CCCC1>[O:21]=[C:19]1[CH:7]2[CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11][N:6]2[CH2:5][CH:4]1[C:3]([O:2][CH3:1])=[O:23]

Komponenten

4

Edukt 2

HCID 23665647Potassium tert-butoxideHCID 86680440HCID 86680440, Verbindung

Produkt 1

HCID 86680441HCID 86680441, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

To a solution of 1-tert-butyl 3-methyl 4-(3-methoxy-3-oxopropyl)piperazine-1,3-dicarboxylate (Example 100A, 180 g, 0.545 mol) in tetrahydrofuran (1.3 L) was added potassium t-butoxide (98 g, 0.872 mol) with stirring at 0-5° C. under N2 atmosphere portion-wise over a period of 30 minutes. The reaction mixture was stirred at ambient temperature for 2 hours. The reaction was then quenched with saturated aqueous ammonium chloride solution (500 mL) and extracted with ethyl acetate (1 L). The organic layer was separated, washed with brine (500 mL), dried over Na2SO4, filtered and concentrated to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 9H), 2.28-2.35 (m, 2H), 2.65-2.83 (m, 1H), 2.83-3.12 (m, 3H), 3.43 (t, 1H, J=8.4 Hz), 3.61 (t, 1H, J=8.4 Hz), 3.78 (s, 3H), 3.98-4.20 (bs, 1H), 4.20-4.45 (bs, 1H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  2. customThe reaction was then quenched with saturated aqueous ammonium chloride solution (500 mL)
  3. extractionextracted with ethyl acetate (1 L)
  4. customThe organic layer was separated
  5. washwashed with brine (500 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-89395c5df5804405981a87d994801d81
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669255B2

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