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

Participants

Reaction Steps

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).

Provenance & Evidence