Cyclobutanone → 4-(4-(1-Cyanocyclobutylamino)phenyl)butanoic acid

Participants

Reaction Steps

Trimethylsilyl cyanide (0.50 g, 5 mmol) was added dropwise to a mixture of 4-(4-aminophenyl)-butyric acid (0.537 g, 3 mmol), cyclobutanone (0.35 g, 5 mmol) and sodium sulfate (1 g) in 1,4-dioxane (10 ml). The mixture was stirred for 15 hours. After filtration to eliminate sodium sulfate, the medium was concentrated under vacuum to obtain a brown liquid which was subjected to chromatography (dichloromethane:acetone, 50:50) to yield 4-[4-(1-Cyanocyclobutylamino)-phenyl]-butyric acid (91) (0.665 g, 2.58 mmol, 86%) as a yellowish solid.

Provenance & Evidence