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

HRID 1751054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1751054
Cl[C:2]1[CH:24]=[CH:23][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)[C:7](=O)[NH:8][C:4]=2[CH:3]=1.Cl[CH2:26][C:27]1[CH:28]=[C:29]([CH:40]=[CH:41][CH:42]=1)[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].[C:43](=O)([O-])[O-:44].[K+].[K+]>CN(C)C=O>[CH2:33]([O:32][C:30]([C:29]1[CH:28]=[C:27]([CH:42]=[CH:41][CH:40]=1)[CH2:26][N:8]1[C:43](=[O:44])[C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:14][CH2:15]2)[N:6]([C:5]2[CH:23]=[CH:24][CH:2]=[CH:3][CH:4]=2)[CH2:7]1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 23024778Benzyl 3-(chloromethyl)benzoateHCID 66652167tert-butyl 4-(5-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 66652022Tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylateAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of tert-butyl 4-(5-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate (637 mg, 1.923 mmol, 1 equiv), benzyl 3-(chloromethyl)benzoate (500 mg, 1.923 mmol, 1 equiv) and potassium carbonate (797.3 mg, 5.769 mmol, 3 equiv) in N,N-dimethylformamide was heated at 65° C. for 16 h. The reaction was partitioned between ethyl acetate and water. The organic layer was further washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified using the Biotage flash chromatography system (SNAP, 50 g cartridge, Rf=0.4, gradient—5%-30% ethyl acetate in hexanes) to afford the tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate as an oil (913 mg, 85.6%). MS for C33H37N3O5 m/z 556.27 (M+H)+.

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was further washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-64a4e8246e5b4492a993d412d2237da6
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156840B2

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