Trifluoroacetic acid → HCID 25254844, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N—BOC-4-hydroxypiperidine (42 mg, 0.21 mmol) in DCM (1 mL) was added TFA (1 mL) at room temperature and the solution was stirred for 0.1 h. The reaction mixture was concentrated under vacuum and dried on the high vacuum pump for 1 h. Example 8a (100 mg, 0.21 mmol) was added and the mixture was suspended in DMF. Cs2CO3 (123 mg, 0.38 mmol) was added in one portion and the solution was heated at 60° C. overnight. The reaction mixture was cooled to room temperature and diluted with water (20 mL) and extracted with EtOAc (3×15 mL), dried over MgSO4 and concentrated under vacuum. The crude material was purified by flash chromatography (silica-gel, MeOH/DCM 1:49) yielding the title compound (51 mg, 47%) as a clear brown oil. 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 7.01-6.95 (m, 2H), 4.12 (m, 2H), 3.95 (t, J=6.6 Hz, 2H), 3.83 (s, 3H), 3.01-2.90 (m, 1H), 2.96-2.68 (m, 4H), 2.50 (s, 3H), 2.18 (s, 3H), 2.05-1.93 (m, 4H), 1.60-1.53 (m, 4H), 1.29 (d, J=6.9 Hz, 3H). MS (ES+) m/z 508 (M+H+).

Provenance & Evidence