Sodium Iodide → HCID 58504420, compound

Participants

Reaction Steps

To a solution of [(2S,5R)-5-methyl-4-(phenylmethyl)-2-morpholinyl]methyl methanesulfonate (8.0 g, 26.7 mmol) in acetone (80 mL) stirred under nitrogen at room temp was added sodium iodide (20.03 g, 134 mmol), and the reaction mixture was stirred at reflux overnight. The reaction was cooled and concentrated under reduced pressure. Then to the residue was added water (50 mL) and CH2Cl2 (60 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (60 mL). The combined organic layers were washed with 1 M Na2S2O3 (2×30 mL), then water (20 mL), dried (Na2SO4), and concentrated to afford the crude product. Purification by silica gel chromatography (300-400 mesh), eluting with Hex/EtOAc (2:1 to 3:2) and monitoring in iodine afforded the title compound (5.9 g) as a yellow oil. LC-MS (ES) m/z=332 [M+H]+.

Provenance & Evidence