Rac-8-benzyl-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one → 4-Phenyl-2,8-diazaspiro[4.5]decan-1-one

HRID 914933Notes

Reaction equation

HRID 914933 reaction equation
C([N:8]1[CH2:24][CH2:23][C:11]2([C:15](=[O:16])[NH:14][CH2:13][CH:12]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.C(Cl)Cl.[Pd]>[C:17]1([CH:12]2[C:11]3([CH2:10][CH2:9][NH:8][CH2:24][CH2:23]3)[C:15](=[O:16])[NH:14][CH2:13]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 21082592Rac-8-benzyl-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one

Product 1

HCID 127097244-Phenyl-2,8-diazaspiro[4.5]decan-1-oneYield 63.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A suspension of rac-8-benzyl-4-phenyl-2,8-diaza-spiro[4.5]decan-1-one (28.8 g, 90 mmol) in MeOH: DCM (4: 1, 500 ml) was hydrogenated in the presence of Pd (10% on C, 14 g, 132 mmol) at 2 bar for 48 h at room temperature. After filtration over celite, the reaction mixture was evaporated and the residue dissolved in NaOH (2 N, 200 mnL). The product was extracted with DCM (3×150 mL) and the combined organic extracts dried over sodium sulfate. Filtration and evaporation afforded the title compound (13.1 g, 63%) as a white solid after trituration from diethylether. MS: m/e=231.4 (M+H).

Workup

  1. filtrationAfter filtration over celite
  2. customthe reaction mixture was evaporated
  3. dissolutionthe residue dissolved in NaOH (2 N, 200 mnL)
  4. extractionThe product was extracted with DCM (3×150 mL)
  5. dry with materialthe combined organic extracts dried over sodium sulfate
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-e881125df20f4cda85628ef8bd2a675d
Source dataset
uspto-grants-2007_09
Patent number
US07265126B2

Reaction notes

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