HCID 68486860, compound → HCID 25019922, compound

Participants

Reaction Steps

A 200 mL flask is charged with (2S)-2-(hydroxymethyl)-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one hydrate (9.37 g, 39.2 mmol) and pyridine (60 mL). The pyridine is removed by rotary evaporation to give (2S)-2-(hydroxymethyl)-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-8-one as a brown paste. The residue is dissolved in fresh pyridine (60 mL), the solution is heated to 30° C., and p-toluenesulfonyl chloride (11.20 g, 58.8 mmol) in toluene (23.5 mL) is added over 30 min. The solution is stirred for 8 h, and then isopropanol (100 mL) is added. The resulting suspension is cooled to 5° C. and the precipitate is collected by vacuum filtration. The filter cake is washed with isopropanol (20 mL) and suction dried to give the title compound (7.81 g, 53%) as a yellow powder. LCMS (Standard Method): 2.50 min, 376 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 10.19 (br s, 1H), 7.76 (d, J=8.1 Hz, 2H), 7.41 (d, J=8.1 Hz, 2H), 6.63 (d, J=8.2 Hz, 1H), 6.27 (d, J=8.2 Hz, H), 4.51-4.46 (m, 1H), 4.32 (dd, J=3.0, 11.3 Hz, 1H), 4.20-4.14 (m, 2H), 3.96 (dd, J=5.9, 11.6 Hz, 1H), 3.13 (ABq, 2H, J=22.3 Hz, Δv=42.4 Hz), 2.38 (s, 3H).

Provenance & Evidence