(Bis(2-methoxyethyl)amino)sulfur trifluoride → 1,1-Dimethylethyl 4-(4-bromophenyl)-4-fluoro-1-piperidinecarboxylate

[Bis(2-Methoxyethyl)amino]sulfur trifluoride (2.1 mL, 11.4 mmol) was added to a stirred solution of 4-(4-bromophenyl)-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (810 mg, 2.28 mmol) in anhydrous DCM (25 mL), at −78° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 72 h. The reaction mixture was quenched by the addition of saturated aqueous potassium carbonate (10 mL) and extracted into DCM (3×10 mL). The combined organic phase was concentrated in vacuo and the residue purified by flash chromatography (silica, 40 g column, ISCO, 0-100% ethyl acetate in cyclohexane) to afford the title compound as a colourless oil (738 mg, 91%). 1H NMR (CDCl3, 300 MHz): 7.50 (d, J=8.5 Hz, 2H), 7.24 (d, J=8.5 Hz, 2H), 4.19-4.05 (m, 2H), 3.29-3.05 (m, 2H), 2.04-1.84 (m, 4H), 1.49 (s, 9H). LCMS (Method B): RT=4.55 min.

1. customThe reaction mixture was quenched by the addition of saturated aqueous potassium carbonate (10 mL)
2. extractionextracted into DCM (3×10 mL)
3. concentrationThe combined organic phase was concentrated in vacuo
4. customthe residue purified by flash chromatography (silica, 40 g column, ISCO, 0-100% ethyl acetate in cyclohexane)

ORD record

ord-d3efe99723be4359bf47fa9f793a42d9

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501765B2