Ammonium Chloride → 3-(Tert-butyldiphenylsilyloxy)propanamidine

Participants

Reaction Steps

To a suspension of NH4Cl (5.35 g, 0.1 mmol) in 60 mL of dry benzend at 0 C was slowly added 50 mL of 2 M solution of trimethylaluminum in toluene. After the addition was complete, the reaction was warmed to RT and was stirred for 2 h until gas evolution had ceased. A solution of 3-(tert-butyl-diphenyl-silanyloxy)-propionitrile (9.27 g, 0.03 mol) in 20 mL of dry benzene was added to the aluminum amide reagent and the resulting was heated up to 80° C. for 20 h. The reaction was slowly cooled to RT and then carefully poured into a slurry of 300 mL of Ch2Cl2 and 200 g of silica gel. It was then filtered and washed thoroughly with MeOH/CH2Cl2 (1:2). After concentration, flash chromatography (SiO2, EtOAc to EtOAc/MeOH=100:20 to 100:30 to EtOAc/2 M NH3 in MeOH=100:30) gave the desired compound as a white solid.

Provenance & Evidence