Tetrahydrofuran → (2-Cyano-5-{[cyano-(8-methoxy-4H-benzo[1,3]-dioxin-6-yl)methyl]amino}benzyl)carbamic Acid t-Butyl Ester

Participants

Reaction Steps

To a mixture of Yb (OTf)3 (0.124 g) and THF (5 mL) there were added (5-amino-2-cyanobenzyl)carbamic acid t-butyl ester (Example (1g))(0.494 g), 8-methoxy-4H-benzo[1,3]dioxine-6-carboaldehyde (0.388 g), MS3A (0.5 g) and trimethylsilyl cyanide (0.533 mL) in that order under a nitrogen atmosphere, and the mixture was stirred at room temperature for 15 hours. Ethyl acetate (100 mL) and water (50 mL) were added to the mixture and filtration was performed with Celite. After sufficiently shaking the filtrate, the organic layer was separated off 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 (0.822 g) as a colorless solid.

Provenance & Evidence