Lithium borohydride → 2-(4-tert-butylphenyl)-N-{(S)-[1-(2-hydroxy-1,1-dimethylethyl)-1H-1,2,3-triazol-4-yl][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}acetamide

Participants

Reaction Steps

To a solution of 0.06 g (0.11 mmol) methyl 2-(4-{(S)-{[(4-tert-butylphenyl)-acetyl]amino}[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}-1H-1,2,3-triazol-1-yl)-2-methylpropanoate in 0.50 ml THF at rt was added 0.13 ml (0.26 mmol) 2.0 M lithium borohydride in THF. After 2 h at room temperature, the reaction-mixture was quenched with a few drops of water and concentrated in vacuo. Purification by preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18) afforded 0.02 g (40%) 2-(4-tert-butylphenyl)-N-{(S)-[1-(2-hydroxy-1,1-dimethylethyl)-1H-1,2,3-triazol-4-yl][5-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}acetamide. ES-MS [M+1]+=520.2. 1H NMR (CDCl3, 400 MHz) δ 8.27 (d, 1H, J=2.83 Hz), 7.78 (br d, 1H, J=6.78 Hz), 7.57 (s, 1H), 7.49 (d, 1H, J=8.60 Hz), 7.39-7.36 (dd, 1H, J=2.93 Hz, 19.7 Hz), 7.36-7.23 (dd, 4H, J=8.24 Hz, 51.4 Hz), 6.36 (d, 1H, J=7.24 Hz), 4.41 (q, 2H, J=7.87 Hz), 3.83 (s, 2H), 3.62 (s, 2H), 1.56 (d, 6H, J=2.29 Hz), 1.31 (s, 9H).

Provenance & Evidence