Azobisisobutyronitrile → HCID 57179453, compound

Participants

Reaction Steps

(E)-Ethyl 3-(1-ethoxycarbonylcyclobutyl)-2-butenoate (16.91 g, 70 mmol) was dissolved in chloroform (180 ml) and N-bromosuccinimide (12.53 g, 70 minol) and a catalytic amount of azobisisobutyronitrile were added thereto. The thus obtained mixture was heated under ref lux for 18 hours. After completing of the reaction, the solvent was evaporated and carbon tetrachloride (100 ml) was added to the residue. Then, insoluble matter was filtered off and the filtrate was concentrated. The residue was dissolved in ethanol (100 ml) and sodium hydrogencarbonate (11.82 g, 140 mmol) was added thereto. Next, (S)-phenylethylamine (9.87 ml, 77 mmiol) was added dropwise thereinto at room temperature. After completing the addition, the resultant mixture was heated under reflux for 3 hours. After completing the reaction, the solvent was evaporated and methylene chloride (300 ml) was added to the residue. The insoluble matter was filtered off and the solvent was evaporated. The residue thus obtained was subjected to silica gel column chromatography (eluent: n-hexane:ethyl acetate=1:1) to obtain 19.57 g (43% of the title compound as an oily substance.

Provenance & Evidence