Trifluoroacetic acid → HCID 24994334, compound

Participants

Reaction Steps

1,1-Dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (prepared as in Example 73, 0.132 g, 0.30 mmol) was dissolved in CH2Cl2 (9 mL). TFA (0.30 mL) was added to this solution and the mixture was stirred at ambient temperature overnight. The excess TFA and CH2Cl2 were removed under reduced pressure. The residue was redissolved in CH2Cl2 (9 mL). The solution was cooled to 0° C. in an ice bath, and diisopropylethylamine (1.5 mL) was added, followed by addition of isopropyl chloroformate (1.0M in toluene, 0.36 mL, 0.36 mmol). The reaction mixture was allowed to warm to ambient temperature, and stirred for 2 h, then diluted with EtOAc, washed with water and brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a light yellow solid. The crude product was purified by chromatography on a silica gel column eluted with 9:4 EtOAc/hexane to give 0.12 g (93%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.40 (d, 1H, J=2.7 Hz), 8.14 (d, 2H, J=8.3 Hz), 8.01 (d, 2H, J=8.6 Hz), 7.74 (d, 1H, J=8.8 Hz), 7.35-7.25 (m, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.23 (bs, 2H), 3.92 (d, 2H, J=6.3 Hz), 3.08 (s, 3H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (APCI), m/z 433 (M+H).

Provenance & Evidence