Pyridine → Benzyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 2362868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2362868
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>ClCCl>[O:17]=[C:10]1[C:11]2([CH2:12][CH2:13][N:14]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:15][CH2:16]2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][NH:9]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-one

Produkt 1

HCID 58046755Benzyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (5 g, 21.6 mmol) in dichloromethane (50 mL) and pyridine (3.5 mL, 43.2 mmol, d=0.978), was added benzyl chloroformate (3.15 mL, 22.04 mmol, d=1.195). After stirring at room temperature for 16 hours, the reaction mixture was diluted with dichloromethane (100 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgSO4, filtered and concentrated to cream solid (6 g, 76%); 1H NMR (DMSO-d6): δ 1.65 (d, 2H, J=13.6 Hz), 2.32-2.40 (m, 2H), 3.51 (br, 2H), 3.95-3.99 (m, 2H), 4.59 (s, 2H), 5.11-5.15 (m, 2H), 6.68 (d, 2H, J=8 Hz), 6.75 (t, 1H, J=7.2 Hz), 7.18 (t, 2H, J=7.6 Hz), 7.30-7.38 (m, 5H), 8.81 (s, 1H); MS for C21H23N3O3 m/z 366 (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 to cream solid (6 g, 76%)

Quellen und Nachweise

ORD-Eintrag
ord-8c72f41b90f843d1b737bc1ce2d58022
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691836B2

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