Trifluoroacetic acid → HCID 57210991, compound

Participants

Reaction Steps

A solution of 188 mg (0.56 mmol) of 4-(3-(4-fluorophenyl)-3-oxo-propyl)-1-(t-butoxycarbonyl) piperidine (from EXAMPLE 189, Step A) in 5 mL of CH2Cl2 at 0° C. was treated with 3 mL of TFA and the resulting mixture was stirred cold for 30 min. The solution was concentrated. A solution of the crude piperidine in 5 mL THF/5 mL of 1.0 N NaOH at 0° C. was treated with 0.09 mL (0.63 mmol) of benzyl chloroformate and the resulting mixture was stirred cold for 30 min. The reaction mixture was partitioned between 50 mL of ether and 10 mL of H2O and the layers were separated. The organic layer was washed with 10 mL of sat'd NaCl, dried and concentrated. Flash chromatography on 10 g of silica gel using 2:1 v/v hexanes/ether as the eluant afforded 196 mg (95%) of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.10-1.20 (m, 21), 1.43-1.53 (m, 1H), 1.60-1.71 (4H), 2.72-2.82 (m, 2H), 2.97 (t, J=7.5, 21), 4.154.21 (m, 2H), 5.12 (s, 2H), 7.11-7.15 (m, 2H), 7.26-7.36 (5H), 7.96-8.00 (m, 2H).

Provenance & Evidence