Water → HCID 118159247, compound

Temperature

23 °C

A mixture of basic alumina (3.0 g, 29.4 mmol) in water (0.6 mL) was stirred at 23° C. for 5 min. Next, ACN (12 mL) was added followed by a solution of tert-butyl 4-((3-fluorophenyl)thio)piperidine-1-carboxylate (1.115 g, 3.58 mmol) in CHCl3 (8 mL). Next, Oxone® (6.60 g, 10.74 mmol) was added and the reaction mixture was stirred at 60° C. for 19 h. The reaction mixture was cooled to 23° C., filtered, rinsed with CHCl3, and the filtrate was washed with water (10 mL). The organic layer was dried over Na2SO4, filtered, rinsed with CHCl3, and dried in vacuo. The crude residue was dissolved in toluene (5 mL) and purified via medium pressure chromatography using a gradient of 10% to 100% EtOAc with 0.1% triethylamine in heptane on a 80 g silica gel column (Single Step™) gave tert-butyl 4-((3-fluorophenyl)sulfonyl)piperidine-1-carboxylate (0.769 g, 62.5%) as a white solid. ESI-MS m/z [M+Na]+ 365.9.

1. stirringthe reaction mixture was stirred at 60° C. for 19 h
2. temperatureThe reaction mixture was cooled to 23° C.
3. filtrationfiltered
4. washrinsed with CHCl3
5. washthe filtrate was washed with water (10 mL)
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. washrinsed with CHCl3
9. customdried in vacuo
10. dissolutionThe crude residue was dissolved in toluene (5 mL)
11. custompurified via medium pressure chromatography

ORD record

ord-aaa9e66d69d14ad099a9dd3e169235ce

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181249B2