Potassium Sodium Tartrate → 3-{[5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]methyl}cyclobutane-1-carbaldehyde

Participants

Reaction Steps

DIBAL (0.69 ml, 0.69 mmol, 1M in THF) was added dropwise to a solution of N-methoxy-N-methyl-3-{[5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]methyl}cyclobutane-1-carboxamide in THF at −10° C. whilst stirring. The reaction was continued for 3 hours at −10° C. The reaction mixture was poured onto sat. aq. Rochelle's salt (20 ml), diluted with Et2O (50 ml) and stirred for 30 min. This was then separated and the organic layer was washed with Rochelle's salt (30 ml), sat. NaHCO3, (30 ml) and brine (30 ml). This was dried over Na2SO4, filtered and evaporated to give a colorless gum (190 mg, 87%); MS (ESI+) for C20H27F3N2O2Si m/z 413.6 [M+H]+; HPLC purity 87% (ret. time, 2.25 min); 1H NMR (500 MHz, CHLOROFORM-d) δH ppm −0.10-0.09 (9 H, m), 0.88-1.00 (4 H, m), 1.63-1.97 (2 H, m), 2.07-2.23 (2 H, m), 2.24-2.37 (0 H, m), 2.37-2.42 (1 H, m), 2.43-2.66 (2 H, m), 2.93-3.34 (4 H, m), 5.49-5.61 (2 H, m), 7.16-7.31 (2 H, m), 7.32-7.32 (2 H, m), 7.49-7.61 (1 H, m), 7.73 (1 H, s), 7.83 (1 H, d, J=8.35 Hz).

Provenance & Evidence