Cyclohexene → 1-[2-(3,8-Diazaspiro[5.5]undecan-3-yl)-2-oxo-ethyl]-3-isobutyl-urea

HRID 2284873Notes

Reaction equation

HRID 2284873 reaction equation
[CH2:1]([NH:5][C:6]([NH:8][CH2:9][C:10]([N:12]1[CH2:32][CH2:31][C:15]2([CH2:20][N:19](C(OCC3C=CC=CC=3)=O)[CH2:18][CH2:17][CH2:16]2)[CH2:14][CH2:13]1)=[O:11])=[O:7])[CH:2]([CH3:4])[CH3:3].C1CCCCC=1>C(O)C.[Pd]>[CH2:16]1[C:15]2([CH2:31][CH2:32][N:12]([C:10](=[O:11])[CH2:9][NH:8][C:6]([NH:5][CH2:1][CH:2]([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:14]2)[CH2:20][NH:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 118045068HCID 118045068, compound

Product 1

HCID 1180213681-[2-(3,8-Diazaspiro[5.5]undecan-3-yl)-2-oxo-ethyl]-3-isobutyl-ureaYield 106.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Suspend benzyl 9-[2-(isobutylcarbamoylamino)acetyl]-2,9-diazaspiro[5.5]undecane-2-carboxylate (239.78 mmoles; 106.60 g) in ethanol (852.80 mL) and cyclohexene (1.20 moles; 121.90 mL), and add 5% palladium on charcoal (24 g; 55.4% moisture content). Heat the mixture to reflux and stir for 45 mins. Cool the mixture to room temperature, filter through a pad of diatomaceous earth washing the solid with ethanol, and concentrate under reduced pressure to give the final title compound, 1-[2-(4,9-diazaspiro[5.5]undecan-9-yl)-2-oxo-ethyl]-3-isobutyl-urea (79.2 g; 94% purity; 100% yield) mass spectrum (m/z):311.2 (M+1).

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. filtrationfilter through a pad of diatomaceous earth
  4. washwashing the solid with ethanol
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-13dd299d0c9941d5bb47741cfd3e6a77
Source dataset
uspto-grants-2015_09
Patent number
US09145437B2

Reaction notes

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