Cyanamide → HCID 86624875, compound

Participants

Reaction Steps

To 8-oxabicyclo[3.2.1]octan-2-one (prepared as described in Vogel et al. Tetrahedron 1993, 49 (8), 1649-1664) (1.1 g, 9.0 mmol) in cyclohexane (10 mL) was added pyrrolidine (0.78 mL, 9.4 mmol) and p-TsOH.H2O (0.085 g, 0.45 mmol). The flask was equipped with a Dean-Stark trap that was pre-filled with cyclohexane. The mixture was warmed to reflux and was allowed to stir for 18 hours with the Dean-Stark trap. This mixture was concentrated and redissolved in methanol (15 mL). Sulfur (0.29 g, 9.0 mmol) was added and the mixture stirred for 15 min. Cyanamide (0.38 g, 9.0 mmol) was then added and the mixture was stirred for 72 hours at ambient temperature. The crude mixture was concentrated under reduced pressure and purified by flash column chromatography (SiO2, 20% hexanes in ethyl acetate) to give the title compound (0.75 g, 4.1 mmol, 46% yield). MS (DCI/NH3) m/z 183 (M+H)+.

Provenance & Evidence