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

HRID 491472Notes

Reaction equation

HRID 491472 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6bf8d4cb5fab4e6f8501cf33cdb0a427
Source dataset
uspto-grants-2009_05
Patent number
US07531546B2

Reaction notes

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