Trifluoroacetic acid → Ethyl 3-fluoro-4-piperidinylacetate

Participants

Reaction Steps

To a solution of ethyl 1-tert-butoxycarbonyl-3-fluoro-4-piperidinylacetate (653 mg, 2.26 mmol) in CH2Cl2 (10 mL) was added TFA (5 mL) at 0° C. After being stirred at room temperature for 4 hr, the reaction mixture was concentrated. The residue was taken up with sat. NaHCO3 solution and extracted with THF-EtOAc (1:1, v/v). The extracts were dried over MgSO4 and concentrated to afford ethyl 3-fluoro-4-piperidinylacetate (420 mg, 98%) as a yellow oil. 1H-NMR (CDCL3) δ 1.26 (t, J=7.4 Hz, 3H), 1.68–1.80 (m, 2H), 2.18 (m, 1H), 2.32 (dd, J=16.6, 6.8 Hz, 1H), 2.54 (dd, J=16.6, 7.5 Hz, 1H), 2.82 (m, 1H), 2.90, 3.00 (each d, J=14.4 Hz, total 1H), 3.31 (m, 1H), 3.51 (m, 1H), 4.15 (q, J=7.4 Hz, 2H), 4.82, 4.71 (each broad s, total 1H).

Provenance & Evidence