Sodium hydride → tert-Butyl 1-(2,2,2-trifluoroethyl)piperidin-4-ylcarbamate

Temperature

0 °C

Into a 50-mL 3-necked round-bottom flask, was placed tert-butyl N-(piperidin-4-yl)carbamate (2 g, 9.99 mmol, 1.00 equip), tetrahydrofuran (20 mL), To this was added sodium hydride (480 mg, 20.00 mmol, 2.00 equip) at 0° C. The resulting solution was stirred for 0.5 h at 0° C., and 2,2,2-trifluoroethyl trifluoromethanesulfonate (2.784 g, 11.99 mmol, 1.20 equip) was added. The resulting solution was stirred for 2 h at 0° C. The reaction was then quenched by the addition of water (100 mL). The resulting solution was extracted with ethyl acetate (3×50 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The filtrate was concentrated under vacuum to yield tert-butyl N-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]carbamate as yellow oil. LCMS (ES, m/z) 283 [M+H]+

1. customInto a 50-mL 3-necked round-bottom flask, was placed
2. stirringThe resulting solution was stirred for 2 h at 0° C
3. customThe reaction was then quenched by the addition of water (100 mL)
4. extractionThe resulting solution was extracted with ethyl acetate (3×50 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe solids were filtered out
7. concentrationThe filtrate was concentrated under vacuum

ORD record

ord-fa680b6487b649eb8f7e3f7745696475

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266835B2