Ethyl Acetate → HCID 178484147, compound

Participants

Reaction Steps

A solution on intermediate 1,4-(pyrrolidin-1-ylmethyl)phenol (5.5 g, 62 mmol) and potassium tert-butoxide (3.5 g, 31 mmol) in DMSO (100 mL) was heated to 100° C. under vigorous stirring in a flow of argon. The mixture was stirred at this temperature for 15 min. A solution of compound 8 (4.5 g, 15.5 mmol) in DMSO (100 mL) and tetrabutylammonium bromide (1.5 g, 9 mmol) were added. The mixture was stirred at 100° C. for 1 h and cooled. The residue was dissolved in EtOAc (200 mL). The solution was washed with water (300 mL), 1 N NaOH (2×100 mL), brine, dried with Na2SO4, and evaporated. The residue was purified by chromatography (silica gel, 63/100 μm, 60 g, CHCl3/hexane 20:80→100:0, CHCl3/MeOH 100:0→80:20 to furnish the title compound (5.56 g, 96%). 1H NMR-data (DMSO-d6): 7.17 (d, 2H, Ph, J=8.6); 6.73 (d, 2H, Ph, J=8.6); 4.68-4.85 (m, 1H); 3.47 (s, 2H, CH2); 3.33 (d, 2H, CH2, J=7.8); 2.78 (s, 3H, NCH3); 2.50-2.60 (m, 1H); 2.33-2.44 (m, 4H); 2.00-2.27 (m, 4H); 1.62-1.71 (m, 4H); 1.38 (s, 9H, Boc).

Provenance & Evidence