Dichloromethane → 3-(Tert-butyldiphenylsilyloxy)propanamidine

Participants

Reaction Steps

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

Provenance & Evidence