(Bis(2-methoxyethyl)amino)sulfur trifluoride → 1-Piperidinecarboxylic acid, 4-(4-cyanophenyl)-4-fluoro-, 1,1-dimethylethyl ester

Temperature

-78 °C

To a stirred solution of compound 1.2 (5 g, 16.54 mmol, 1.00 equiv) in dichloromethane (250 mL) under nitrogen at −78° C. was added dropwise Deoxo-Fluor® (4.4 g, 19.89 mmol, 1.20 equiv). The resulting mixture was stirred for 1 h at −78° C. The reaction mixture was then carefully quenched by the addition of 50 mL of sodium bicarbonate (aq.sat.) and extracted with 3×100 mL of dichloromethane. The combined organic layers were washed with 150 mL of brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:30) as eluent to yield 2.5 g (35%) of the title compound as a white solid.

1. customThe reaction mixture was then carefully quenched by the addition of 50 mL of sodium bicarbonate (aq.sat.)
2. extractionextracted with 3×100 mL of dichloromethane
3. washThe combined organic layers were washed with 150 mL of brine
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified

ORD record

ord-0b8aeb7d9af84260a5b2e3a566d8a664

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2