Anisole → HCID 10236740, compound

Participants

Reaction Conditions

Reaction Steps

The compound of Example 19 (0.585 mg, 1.38 mmol) was dissolved in methylene chloride (2 mL) and cooled to 0° C. Trifluoromethane sulfonic acid (0.853 mL, 9.63 mmol) and anisole (0.449 mL, 4.13 mmol) were then added. The reaction mixture was stirred at 0° C. for 5 minutes and then held at room temperature for 1 hour. The reaction mixture was again cooled to 0° C. and the pH was adjusted until basic with 1N NaOH. The reaction mixture was transferred to a separatory funnel with methylene chloride and water, and extracted with methylene chloride (4×). The combined organic layers were then dried with magnesium sulfate, filtered and concentrated to give a yellow oil (0.584 g crude). Further purification (5% ammonia in 2M solution of methanol/ethyl acetate) yielded 0.336 g of the free amine product (84%). The free amine (0.392 g, 1.35 mmol) was dissolved in diethyl ether and HCl in 2M solution of diethyl ether (0.740 mL, 1.48 mmol) was added. After stirring for 30 minutes, the solid was filtered and air dried.

Provenance & Evidence