Lawesson's reagent → HCID 90442641, compound

Participants

Reaction Steps

To a solution of tert-butyl 2-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate (733 mg, 3.05 mmol) in THF (10 mL) was added Lawesson's reagent (700 mg, 1.68 mmol). The mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was dissolved in EtOAc and washed 3× with saturated aqueous NaHCO3 solution. The combined aqueous layers were extracted several times with EtOAc and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on SiO2 eluting with EtOAc/Hex to afford the title compound as a colorless foam (622 mg, 79%). MS (ESI): mass calcd. C12H20N2O2S, 256.12; m/z found, 257.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.54-8.20 (m, 1H), 5.23-4.97 (m, 1H), 4.66-4.33 (m, 1H), 3.81-3.63 (m, 1H), 3.28-3.17 (m, 1H), 2.22-2.11 (m, 1H), 1.90-1.58 (m, 5H), 1.47 (s, 9H).

Provenance & Evidence