Potassium Carbonate → Tert-butyl 3-(6-(benzyloxy)-6-oxohexyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 2362879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2362879
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[N:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4][NH:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38]>CN(C)C=O.C(OCC)(=O)C>[CH2:40]([O:39][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][N:3]1[C:2](=[O:1])[C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[N:5]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:4]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 389488tert-Butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylateHCID 562258Benzyl 6-bromohexanoate

Produkt 1

HCID 58046758Tert-butyl 3-(6-(benzyloxy)-6-oxohexyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylateAusbeute 12,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of tert-butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.4 g, 1.2 mmol) and potassium carbonate (0.25 g, 1.8 mmol) in N,N-dimethylformamide (5 mL), was added benzyl 6-bromohexanoate (0.34 g, 1.2 mmol). After stirring at 55° C. for 18 hours, the reaction mixture was diluted with ethyl acetate (25 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to obtain the title compound (0.08 g, 12%); MS for C31H41N3O5 m/z 536.16 (M+H)+.

Aufarbeitung

  1. washwashed with dilute citric acid, water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d675f4cd6628432ea79c1a52a14dd406
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691836B2

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