Benzyl Chloride → HCID 68839424, Verbindung

HRID 227254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 227254
[H-].[Na+].[CH2:3]([CH:10]1[NH:14][C:13]2([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[NH:12][C:11]1=[O:27])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[NH4+].[Cl-]>C1COCC1>[CH2:28]([N:12]1[C:13]2([CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:18][CH2:19]2)[NH:14][CH:10]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:11]1=[O:27])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

6

Edukt 4

HCID 7503Benzyl Chloride2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 68839899Tert-butyl 3-benzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

Produkt 1

HCID 68839424HCID 68839424, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

NaH (1.26 g, 52.5 mmol) was added to a solution of tert-butyl 3-benzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate (12.1 g, 35 mmol) in THF (250 ml) at RT. After stirring for 1 h at 0° C., benzyl chloride (4.9 g, 38.5 mmol) was added dropwise, and the mixture was allowed to warm to RT and heated under reflux for 60 h. Subsequently, benzyl chloride (2.4 g, 19 mmol) was again added, and the mixture was heated under reflux for a further 16 h. The reaction mixture was treated with saturated aqueous NH4Cl solution (20 ml) and extracted with EA (3×50 ml). The combined organic phase was dried over Na2SO4 and filtered and the solvent was removed by distillation. Workup was carried out by means of column chromatography to give tert-butyl 1,3-dibenzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate in a yield of 13.5 g (88% of theory).

Aufarbeitung

  1. temperatureto warm to RT
  2. temperatureheated
  3. temperatureunder reflux for 60 h
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for a further 16 h
  6. extractionextracted with EA (3×50 ml)
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was removed by distillation

Quellen und Nachweise

ORD-Eintrag
ord-c63f8e9012b947eb9d37ea643e6929ff
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560468B2

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