Ethanol → 2,8-Diazaspiro[4.5]decane-1,3-dione

HRID 491472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491472
C([N:8]1[CH2:19][CH2:18][C:11]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[CH2:12]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.CCO>[OH-].[OH-].[Pd+2].C(O)(=O)C>[C:15]1(=[O:16])[C:11]2([CH2:10][CH2:9][NH:8][CH2:19][CH2:18]2)[CH2:12][C:13](=[O:17])[NH:14]1

Komponenten

5

Edukt 2

HCID 702EthanolHCID 221109398-Benzyl-2,8-diazaspiro[4.5]decane-1,3-dione

Produkt 1

HCID 156710412,8-Diazaspiro[4.5]decane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To 8-benzyl-2,8-diaza-spiro[4.5]decane-1,3-dione (28.3 g, 0.11 mol) and Pd(OH)2 (8.5 g) in 2 l of flask, EtOH (438 ml) and acetic acid (5.5 ml) are added at ambient temperature. The reaction mixture is stirred under H2 at room temperature for 15 h. The catalysts are removed by filtration and EtOH is evaporated down to give 2,8-diaza-spiro[4.5]decane-1,3-dione in quantitative yield. To a suspension of 2,8-diaza-spiro[4.5]decane-1,3-dione (4.2 g, 25.2 mmol) in dichloromethane (60 ml), 1N NaOH (26 ml, 26 mmol) and di-t-butyldicarbonate (6.1 g, 27.7 mmol) in dichloromethane (20 ml) are added at ambient temperature. The reaction mixture is stirred for 15 h. 10% Citric acid is added to the reaction mixture and the pH of the mixture is adjusted to 5. The combined extracts are washed with brine, dried over magnesium sulfate and concentrated under vacuum to give solid product, which filtrated with diethyl ether.

Aufarbeitung

  1. customThe catalysts are removed by filtration and EtOH
  2. customis evaporated down

Quellen und Nachweise

ORD-Eintrag
ord-6bf8d4cb5fab4e6f8501cf33cdb0a427
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531546B2

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