Ethanol → N-[5-(2-{4-[4-(4-Aminobutyl)phenyl]-1-methylbutylamino}-1-(R)-hydroxyethyl)-2-hydroxyphenyl]formamide

Participants

Reaction Steps

A mixture of compounds 27 (029 g, 0.45 mmol), palladium catalyst (0.2 g, 10% Pd on carbon, 50% wet), ethanol (10 mL) and methanol (5 mL) underwent hydrogenation at room temperature for 4 h under one H2 pressure. The catalyst was vacuum filtered and washed with ethanol (3×5 mL). The filtrate and the washings were combined and concentrated. The residue was subjected to column chromatography, eluting with a mixture of methanol (0-22%), concentrated ammonium hydroxide (0-2.2%) and dichloromethane (100-75.6%), to afford the desired product 28 (0.10 g, 54%) as a colorless, glass solid: 1H NMR (300 MHz, CD3OD) δ 1.08 (d, 3H), 1.32 (m, 2H), 1.48-1.78 (m, 6H), 2.59 (m, 4H), 2.78 (m, 5H), 3.44 (m, 2H), 4.75 (m, 1H), 6.82 (m, 1H), 7.00 (m, 1H), 7.08 (m, 5H), 8.06 (s, 1H), 8.31 (s, 1H); m/z (ESI) 414 [C31H41N3O3+H]+. The diastereoisomer 29 (13 mg, 7%) was also isolated as a light yellow solid: 1H NMR (300 MHz, CD3OD) δ 1.26 (d, 3H), 1.48-1.90 (m, 8H), 2.50 (m, 4H), 2.82-3.08 (m, 3H), 3.50 (m, 2H), 4.60 (m, 1H), 6.82-6.82 (m, 2H), 7.10 (m, 5H), 8.00 (s, 1H), 8.28 (s, 1H); m/z (ESI) 414 [C31H41N3O3+H]+.

Provenance & Evidence