Triethylamine → 3-Methoxy-cyclobutylmethylazide

530 μl of triethylamine followed by 220 μl of methanesulfonylchloride were added under iced temperature to 220 mg of 1) 3-methoxy-cyclobutylmethanol obtained in the above 1). The mixture was heated to room temperature and stirred for 30 min. The reaction solution was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate water and saturated saline solution, and dried with anhydrous sodium sulfate. The residues obtained by evaportating the solvents under reduced pressure were dissolved in 4 ml of dimethylformamide. Then, 245 mg of sodium azide was added, and the mixture was stirred at 80° C. for 1.5 hours. The reaction solution was diluted with ethyl acetate, washed with water and saturated saline solution and dried with anhydrous sodium sulfate. The residues obtained by distilling out the solvents under reduced pressure were separated and purified by silicagel column chromatography (ethyl acetate:hexane=10:90) to obtain 195 mg of the above compound.

1. customobtained in the above 1)
2. washwashed with water, saturated sodium bicarbonate water and saturated saline solution
3. dry with materialdried with anhydrous sodium sulfate
4. customThe residues obtained
5. stirringthe mixture was stirred at 80° C. for 1.5 hours
6. washwashed with water and saturated saline solution
7. dry with materialdried with anhydrous sodium sulfate
8. customThe residues obtained
9. distillationby distilling out the solvents under reduced pressure
10. customwere separated
11. custompurified by silicagel column chromatography (ethyl acetate:hexane=10:90)

ORD record

ord-bf530e4ce0074f84884d1ad667b1d969

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902369B2