1,2-Dichloroethane → Tert-butyl 2-(4-(methoxymethyl)-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1848502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848502
[OH:1][CH2:2][C:3]1[C:7](=[O:8])[O:6][CH2:5][C:4]=1[N:9]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:10]1=[O:26].CI.Cl[CH2:30]CCl>C(Cl)Cl.[Ag]=O>[CH3:30][O:1][CH2:2][C:3]1[C:7](=[O:8])[O:6][CH2:5][C:4]=1[N:9]1[CH2:13][CH2:12][C:11]2([CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:17][CH2:18]2)[C:10]1=[O:26]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 6328Methyl iodide2×HCID 86709511Tert-butyl 2-(4-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Produkt 1

HCID 86709512Tert-butyl 2-(4-(methoxymethyl)-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysator2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-butyl 2-(4-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (0.42 g, 1.15 mmol), silver oxide (0.292 g, 1.26 mmol) and methyl iodide (0.358 mL, 5.73 mmol) were taken up in DCM (5 mL) and stirred over night at room temperature under nitrogen. Additional silver oxide (0.292 g, 1.26 mmol) and methyl iodide (0.358 mL, 5.73 mmol) were added to the mixture with DCE (8 mL) and the resulting mixture was heated at 54° C. overnight. The reaction mixture was filtered through CELITE® to remove silver oxide, concentrated, and purified by silica gel column chromatography (40 g RediSep Gold column) using (20-80) % EtOAc/DCM as mobile phase to afford the title compound.

Aufarbeitung

  1. temperaturethe resulting mixture was heated at 54° C. overnight
  2. filtrationThe reaction mixture was filtered through CELITE®
  3. customto remove silver oxide
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (40 g RediSep Gold column)

Quellen und Nachweise

ORD-Eintrag
ord-730b9eb2d3154803b68dbfafbaeab478
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952166B2

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