Cyanamide → HCID 86624874, compound

Participants

Reaction Conditions

Reaction Steps

To 8-oxabicyclo[3.2.1]oct-6-en-2-one (prepared as described in Vogel et al. Tetrahedron 1993, 49 (8), 1649-1664) (0.5 g, 4.0 mmol) in cyclohexane (3 mL) in a sealable tube was added pyrrolidine (1.7 mL, 20.1 mmol) followed by MgSO4 (4.8 g, 40.3 mmol). The tube was sealed and the mixture was warmed to 100° C. and stirred for 16 hours. The reaction mixture was cooled to ambient temperature, filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in 10 mL methanol, sulfur (0.13 g, 4.0 mmol) was added and the mixture stirred for 20 min. Cyanamide (0.17 g, 4.0 mmol) was then added and the mixture stirred at ambient temperature for 48 hours. The reaction mixture was concentrated under reduced pressure and purified by flash column chromatography (SiO2, 50% hexanes in ethyl acetate) to give the title compound (90 mg, 0.5 mmol, 12% yield). 1H NMR (300 MHz, CDCl3) δ ppm 2.30 (d, J=16.3 Hz, 1H) 3.21 (ddd, J=16.4, 6.0, 1.0 Hz, 1H) 4.64-4.77 (m, 2H) 5.12 (dd, J=5.9, 1.9 Hz, 1H) 5.25-5.29 (m, J=1.9, 1.9 Hz, 1H) 6.00 (dd, J=5.9, 1.9 Hz, 1H) 6.63 (dd, J=5.6, 1.5 Hz, 1H); MS (DCI/NH3) m/z 181 (M+H)+.

Provenance & Evidence