Tetraisopropyl Orthotitanate

Typical Procedure: To the solution of carbonyl compound (1 mmol) in THF (4 mL), the primary or secondary amine (1.2 mmol) is added followed by the addition of Ti(Oi-Pr)4 (1.2 mmol). The reaction mixture is stirred for 1 h at room temperature. Ammonia borane (1.2 mmol) is added and stirring is continued at the same temperature. Upon completion of the reaction, as revealed by TLC, the resulting mixture is treated with HCl (3 mL, 6 M) and stirred for an additional hour. The reaction mixture is diluted with water (10 mL) and extracted with diethyl ether (3 × 15mL). The aqueous layer is then treated with NaOH (2 M) until pH 10-12 and extracted with diethyl ether (3 × 15mL). The combined organic extracts are washed with brine, dried (Na2SO4), concentrated in vacuo, and purified by silica gel flash chromatography to obtain the desired product.