Benzyl Bromide → 4-Methyl-7-(phenylmethyl)-4,7-diazaspiro[2.5]octane-5,8-dione

HRID 1366574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366574
[H-].[Na+].[CH3:3][N:4]1[C:11](=[O:12])[CH2:10][NH:9][C:8](=[O:13])[C:5]21[CH2:7][CH2:6]2.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.O>[CH3:3][N:4]1[C:11](=[O:12])[CH2:10][N:9]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8](=[O:13])[C:5]21[CH2:7][CH2:6]2

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 669363934-Methyl-4,7-diazaspiro[2.5]octane-5,8-dione

Produkt 1

HCID 669362214-Methyl-7-(phenylmethyl)-4,7-diazaspiro[2.5]octane-5,8-dioneAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (302 mg, 12.62 mmol) was taken up in DMF (10 mL) and cooled to 0° C. for 30 min. Then a mixture 4-methyl-4,7-diazaspiro[2.5]octane-5,8-dione (1.769 g, 11.47 mmol) in DMF (5 mL) was slowly added over 10 min. This mixture was allowed to stir for 45 min, and then benzyl bromide (4.08 mL, 34.41 mmol) was added, and the reaction was stirred for 45 min further. The mixture was carefully diluted with water (10 mL) and concentrated in vacuo. The resulting crude product was purified via reverse phase HPLC to provide 4-methyl-7-(phenylmethyl)-4,7-diazaspiro[2.5]octane-5,8-dione (1.535 g, 54%). LCMS: (M+H)+: 245.1.

Aufarbeitung

  1. stirringthe reaction was stirred for 45 min further
  2. concentrationconcentrated in vacuo
  3. customThe resulting crude product was purified via reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3774748bdb24401f94a189838d9348ac
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

Notizen zur Reaktion

Wird geladen…