Sodium Iodide → HCID 58504420, compound

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]+.

1. temperatureat reflux overnight
2. temperatureThe reaction was cooled
3. concentrationconcentrated under reduced pressure
4. additionThen to the residue was added water (50 mL) and CH2Cl2 (60 mL)
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with CH2Cl2 (60 mL)
7. washThe combined organic layers were washed with 1 M Na2S2O3 (2×30 mL)
8. dry with materialwater (20 mL), dried (Na2SO4)
9. concentrationconcentrated
10. customto afford the crude product
11. customPurification by silica gel chromatography (300-400 mesh)
12. washeluting with Hex/EtOAc (2:1 to 3:2)

ORD record

ord-87121bbe983843f79f6f3214023738ff

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697685B2