[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol → Ammonia

Participants

Reaction Conditions

Reaction Steps

A mixture of [2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl) phenyl]methanol (Preparation 23) (800 mg, 1.77 mmol) and 3-[3-(2-amino-2-methyl-propyl)phenyl]-acrylic acid benzyl ester (preparation 142), (1.10 g, 3.55 mmol) was stirred at 90° C. for 18 hours. The reaction mixture was then cooled to room temperature, diluted with diethyl ether (40 mL) and stirred for 4 hours. The resulting precipitate was filtered off, washing though with diethyl ether, and the filtrate was concentrated in vacuo to give a brown oil. Purification of the oil by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia afforded the title compound in 25% yield, 300 mg. 1H NMR (400 MHz, CD3OD) δ: 7.78 (1H, d), 7.38 (16H, m), 6.95 (1H, m), 6.58 (1H, d), 5.25 (2H, s), 5.04 (2H, s), 4.78 (1H, m), 4.64 (2H, m), 2.80 (2H, m), 2.68 (2H, m), 1.14 (3H, s), 1.10 (3H, s), 0.78 (9H, s), −0.03 (3H, s), −0.21 (3H, s) ppm; LRMS ESI m/z 680 [M+H]+

Provenance & Evidence