Ethanol → HCID 18441772, Verbindung

HRID 458155

Reaktionsgleichung

Reaktionsgleichung von HRID 458155
[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[N:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(N(CC)CC)C.C([OH:41])C>>[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][N:16]([CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31][C:26]3=[O:41])[CH2:15][CH2:14]2)[N:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 10952ChlorocyclohexaneHCID 184417443-Benzyl-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

Produkt 1

HCID 18441772HCID 18441772, Verbindung

Versuchsvorschrift

A solution of 0.30 g (0.93 mmol) 3-benzyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one, 0.14 g (1.0 mmol) 2-chlorocyclohexane, and 0.2 ml (1.4 mmol) triethylamine in ethanol was refluxed overnight. The reaction mixture was cooled to ambient temperature, concentrated and then quenched with saturated NaHCO3 and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated. Purification of the crude product over a silica gel plug (10:1) with n-heptane/AcOEt as eluent provided 0.14 g rac-3-benzyl-8-(2-oxo-cyclohexyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one as a light yellow oil; MS (ISP): 418.4 MH+.

Aufarbeitung

  1. concentrationconcentrated
  2. customquenched with saturated NaHCO3
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the crude product over a silica gel plug (10:1) with n-heptane/AcOEt as eluent

Quellen und Nachweise

ORD-Eintrag
ord-36743b9b689d4a9dbc65f524433382d2
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189850B2

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