Methyl iodide → HCID 24220913, compound

To a solution of tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate (0.97 g) in DMF (8.0 mL) was added 1,1′-thiocarbonyldiimidazole (0.86 g), and the mixture was stirred at room temperature for 1 hr. The mixture was heated at 100° C. for 2 hr, cooled to 0° C., and methyl iodide (0.5 mL) was added. The mixture was stirred at 0° C. for 1 hr, diluted with ice water, and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, water and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 0→60% ethyl acetate/hexane) to give tert-butyl 4-[5-(methylsulfanyl)-1,3,4-oxadiazol-2-yl]piperidine-1-carboxylate (1.1 g, 91%) as a yellow oil.

1. temperatureThe mixture was heated at 100° C. for 2 hr
2. temperaturecooled to 0° C.
3. stirringThe mixture was stirred at 0° C. for 1 hr
4. extractionextracted with ethyl acetate
5. washThe extract was washed with 1N hydrochloric acid, water and saturated brine
6. customdried
7. concentrationconcentrated under reduced pressure
8. customThe residue was separated
9. custompurified by silica gel column chromatography (solvent gradient; 0→60% ethyl acetate/hexane)

ORD record

ord-f53a59dc07854e6babdc7af3b3467788

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592454B2