Triethylamine → HCID 131727787, compound

Participants

Reaction Steps

To the imine 15A (1.0 g, 2.84 mmol) and triethylamine (0.39 mL, 2.84 mmol) in dichloromethane (50 mL) at −10° C. was added titanium chloride (11.3 mL, 1.0 M in dichloromethane) dropwise under argon. The reaction was stirred at rt for 4 h and then quenched with saturated potassium carbonate. The mixture was filtered through celite and the aqueous layer was extracted with dichloromethane (2×). The organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was evaporated and the crude residue was purified by preparative HPLC equipped with a YMC ODS S5 (30×100 mm) column. The separation was performed using a linear gradient (solvent A: 10% acetonitrile-90% water-0.1% TFA; solvent B: 90% acetonitrile-90% water-0.1% TFA; 0 to 100% B in 12 min with a flow rate of 40 mL/min to give 0.32 g of 15B as a solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 2.53 (m, 2H) 3.47 (s, 3H) 3.62 (m, 1H) 3.79 (m, 2H) 5.14 (d, J=6.85 Hz, 1H) 7.76 (m, 2H) 8.33 (m, 2H).

Provenance & Evidence