1,1'-Thiocarbonyldiimidazole → HCID 89315765, compound

Participants

Reaction Steps

To a solution of (1R,2R,3S,4S,6S)-3-amino-6-(difluoromethyl)cyclohexane-1,2,4-triol (300 mg, 1.52 mmol) in DMF (3 mL) at room temperature was added thiocarbonyldiimidazole (298 mg, 1.67 mmol). The mixture was stirred at room temperature for 4 h. Solvent was evaporated and the residue was purified by silica gel column chromatography, eluted with 5%-8% MeOH in DCM to give the product (3aR,4R,5R,6S,7aS)-6-(difluoromethyl)-4,5-dihydroxyhexahydrobenzo[d]oxazole-2(3H)-thione (238 mg, 65%) as a white solid. 1H NMR (400 MHz, MeOD) δ 6.20 (t, J=57.4 Hz, 1H), 4.92-4.96 (m, 1H), 3.71 (t, J=7.1 Hz, 1H), 3.26-3.38 (m, 2H), 2.35 (dt, J=15.3 Hz, 3.0 Hz, 1H), 2.03-2.17 (m, 1H), 1.91-1.99 (m, 1H).

Provenance & Evidence