Iodine → 3-[(2R)-tetrahydrofuran-2-ylmethyl]-3,4,5,6,7,8-hexahydro-2H-4,7-epoxycyclohepta[d][1,3]thiazol-2-imine

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A mixture of 8-oxabicyclo[3.2.1]octan-2-one (obtained as described in Vogel et al. Tetrahedron 1993, 49 (8), 1649-1664) (0.53 g, 4.2 mmol), (R)-(tetrahydrofuran-2-yl)methanamine (0.43 mL, 4.2 mmol) and 1 g of 4 Å molecular sieves (8-12 mesh beads) in acetonitrile (4 mL) was stirred at ambient temperature for 16 h. The material was filtered through Celite® with acetonitrile (additional 10 mL) then the filtrate treated with potassium thiocyanate (0.54 g, 5.6 mmol) was added and the mixture was warmed to 50° C. Iodine (2.1 g, 8.4 mmol) was added and the mixture stirred at 50° C. for 72 h. The mixture was cooled to ambient temperature and was concentrated under reduced pressure. The crude material was diluted with 20 mL CH2Cl2 and was stirred with sodium metabisulfite (20 mL of 20% aqueous solution) for 15 min. The layers were separated and the aqueous layer was extracted 3×10 mL CH2Cl2. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude material (1.0 g, 3.8 mmol, 89% yield) which was carried on without further purification. MS (DCI/NH3) m/z 267 (M+H)+.

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