(Diethylamino)sulfur trifluoride → Tert-butyl 3-cyano-3-fluoropiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-cyano-3-hydroxypiperidine-1-carboxylate (5.7 g, 25.1 mmol) in DCM (50 mL) cooled to −78° C., DAST (4.85 g, 30.1 mmol) was added drop-wise and the resulting solution stirred at −78° C. for 1 hour. The reaction was warmed to 0° C. and stirred for an additional 1 hour. The reaction mixture was diluted with DCM and quenched with sat. aq. NaHCO3. The combined extracts were dried by Na2SO4, filtered and concentrated in vacuo to afford crude title compound as a pale yellow oil 5.5 g. MS (m/z): 129 (M+H-Boc)+

Provenance & Evidence