Trimethylsilyl cyanide → HCID 59511834, compound

Participants

Reaction Steps

To a mixture of Yb(OTf)3 (0.399 g) and dichloromethane (20 mL) there were added (5-amino-2-bromobenzyl)carbamic acid t-butyl ester (1.95 g), 3-(t-butyldimethylsilanyloxy)-5-ethyl-2-fluorobenzaldehyde (1.83 g), MS3A (2.6 g) and trimethylsilyl cyanide (1.29 mL) in that order under a nitrogen atmosphere, and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off under reduced pressure, ethyl acetate (200 mL) and water (100 mL) were added to the residue, and after sufficiently shaking the mixture, the organic layer was separated off, washed with saturated aqueous sodium chloride (100 mL) and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (3.09 g) as a colorless solid.

Provenance & Evidence