Water → N-Methyl-N-{2-[(tributylstannyl)methoxy]ethyl}cyclohexaneamine

Temperature

60 °C

To a mixture of sodium hydride (50%, 241 mg, 5.0 mmol) and tetrahydrofuran (20 ml) was added 2-[cyclohexyl(methyl)amino]ethanol (791 mg, 5.0 mmol) at 0° C. (external temperature). Then, the reaction mixture was stirred at 60° C. for 30 minutes. After the reaction mixture was cooled at 0° C. (external temperature), to the reaction mixture was added dropwise a solution of tributyl-iodomethyl-tin (2.2 g, 5.0 mmol) in tetrahydrofuran (5 ml), and the reaction mixture was stirred at 60° C. for 1 hour. After the reaction mixture was cooled at room temperature (external temperature), water was added to stop the reaction. Ethyl acetate was added to the reaction mixture, and the organic layer was separated. After the organic layer was washed with water, an aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel) to obtain the title compound (790.7 mg, 4.3 mmol, 85%).

1. temperatureAfter the reaction mixture was cooled at 0° C. (external temperature)
2. stirringthe reaction mixture was stirred at 60° C. for 1 hour
3. additionwas added
4. customthe reaction
5. customthe organic layer was separated
6. washAfter the organic layer was washed with water
7. distillationan aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure
8. customThe residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel)

ORD record

ord-210dbaacbcd64b4dbdd1bdd888419e6a

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696347B2