Toluene → HCID 131481771, compound

Participants

Reaction Steps

Toluene (250 mL) was added to 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (5.0 g, 21.54 mmol) followed by cyclohexylamine (2.37 g, 23.89 mmol) and formic acid (˜1.0 mL of 88%) to form a clear solution. The mixture was allowed to reflux using a Dean-Stark trap and the toluene/water mixture collected till clear. Upon completion, the mixture was cooled to room temperature and the solution evaporated to 100 mL. MeOH (200 mL) was then added to the reaction mixture followed by NaBH4 (1.63 g, 43.08 mmol) portion wise. The mixture was stirred for 20 min and quenched with water (5 mL). The solution was evaporated to 100 mL and EtOAc (50 mL) was added. The solution was dried with Na2SO4 and the solvent removed by reduced pressure, yielding a white solid. Et2O (200 mL) was then added dissolving half of the white solid. The remaining solid was collected and dried under reduced pressure offering compound 7. Yield: 6.3 g, 46.4%. 1H NMR (CD2Cl2): δ 7.52-7.50 (d, 1H), 7.28-7.27 (m, 2H), 7.15-7.13 (d, 1H), 4.02 (s, 2H), 3.42 (s, 1H), 3.15-3.07 (m, 1H), 1.74-1.61 (m, 5H), 1.29 (s, 12H), 1.19-1.05 (m, 6H).

Provenance & Evidence