2-Thiocresol → HCID 89395585, compound

Participants

Reaction Steps

To a solution of piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (5 g, 21.8 mmol, 1 eq.) and DIEA (7.6 mL, 44 mmol, 2 eq.) in DMF was added HATU (9.12 g, 24 mmol, 1.1 eq.) and stirred at room temperature for 30 min. Methylbenzenethiol (3 g, 24 mmol, 1.1 eq.) in 45 mL of DMF was added and the resulting mixture was stirred at room temperature overnight. After 18 h, the reaction mixture was concentrated in vacuo to give an oil. This oil was purified by silica gel column chromatography (0-20% ethyl acetate/heptane) to give the title compound as a white solid (6.6 g, 90% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.28 (m, 4H), 4.13 (m, 2H), 2.81 (m, 3H), 2.39 (s, 3H), 1.97 (m, 2H), 1.73 (m, 2H), 1.48 (s, 9H), MS (ESI) m/z 336.6 (M+H)+. Exact mass calculated for C18H26N1O3S, 336.2. MS (ESI) m/z 279.9 (M+H without t-butyl). Retention time: 1.27 min (5-95% CH3CN/H2O over 2 min with 0.1% formic acid, Inertsil 3×3 mm C-8-3 column with flow rate of 2 mL/min).

Provenance & Evidence