Water → 2,8-Diazaspiro[4.5]decane-8-carboxylic acid, 2-[(4-bromophenyl)methyl]-1-oxo-, 1,1-dimethylethyl ester

HRID 1182157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182157
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:20][CH2:19][C:13]2([C:17](=[O:18])[NH:16][CH2:15][CH2:14]2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[Br:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.O>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][C:13]2([C:17](=[O:18])[N:16]([CH2:26][C:25]3[CH:28]=[CH:29][C:22]([Br:21])=[CH:23][CH:24]=3)[CH2:15][CH2:14]2)[CH2:19][CH2:20]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 45073946tert-Butyl 1-oxo-2,8-diazaspiro(4.5)decane-8-carboxylate

Produkt 1

HCID 589819962,8-Diazaspiro[4.5]decane-8-carboxylic acid, 2-[(4-bromophenyl)methyl]-1-oxo-, 1,1-dimethylethyl esterAusbeute 111,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

Introduce 600 mg (14.7 mmol) of sodium hydride (60% suspension in mineral oil) in a 500 mL round bottom flask under nitrogen before adding successively 20 mL of anhydrous DMF and 2.5 g (9.8 mmol) of 1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester previously dissolved in 20 mL of anhydrous DMF. After agitating one hour at room temperature, 2.5 g (9.8 mmol) of 4-bromobenzylbromide diluted in 20 mL of anhydrous DMF were added and the reaction mixture was agitated an additional hour at room temperature. Then 100 mL of water were added and the solution was extracted with diethyl ether (2×150 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated under reduced pressure to yield 4.63 g of 2-(4-bromobenzyl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester as a yellow oil.

Aufarbeitung

  1. additionwere added
  2. stirringthe reaction mixture was agitated an additional hour at room temperature
  3. extractionthe solution was extracted with diethyl ether (2×150 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8f926eaf6eec441dbc9e2502f8b92387
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288548B2

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