tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((4-octylphenylamino)methyl)propane-1,3-diol

Participants

Reaction Steps

A solution of a product of Step A (0.32 g; 0.71 mmol) in 60% trifluoroacetic acid in CH2Cl2 (4 ml) was stirred for 15 min at room temperature then diluted to 6 ml with methanol (MeOH). The resulting mixture was evaporated to dryness under reduced pressure and the residue dried in vacuo for 1 h. This was purified by flash column chromatography (FCC) (SiO2; CH2Cl2 saturated with NH4OH:MeOH 95:5), to give pure title compound (0.18 g; 82%), as colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 2H, J=6.96 Hz); 1.25 (m, 10H); 1.52 (m, 2H); 2.1-2.51 (broad m, 4H); 2.47 (tr, 2H, J=7.9 Hz); 3.1 (s, 2H); 3.55 (m, 4H); 4.05 (broad s, 1H); 6.6 (d, 2H, J=8.34 Hz); 6.96 (d, 2H, J=8.34 Hz).

Provenance & Evidence