[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), (900 mg, 2 mmol) and N-1-adamantyl-2-{3-[(2R)-2-aminopropyl]pheny}acetamide (preparation 163), (1.3 g, 4 mmol) were heated at 90° C. for 24 hours. The reaction mixture was then cooled to room temperature and the crude product was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 95:5:0.5, to afford the title compound as a pale foam in 83% yield, 1.16 g. 1H NMR (400 MHz, CD3OD) δ: 7.48-7.28 (6H, m), 7.17-6.72 (6H, m), 5.14 (2H, s), 4.78-4.74 (1H, m), 4.73-4.64 (m, 2H), 3.36 (2H, s), 2.95-2.84 (2H, m), 2.70-2.63 (2H, m), 2.59-2.50 (1H, m), 2.03 (3H, m), 2.00 (6H, m), 1.70-1.64 (6H, m), 1.05 (3H, d), 0.84 (9H, s), 0.00 (3H, s), −0.18 (3H, s) ppm.

Provenance & Evidence