1-Bromo-4-phenylmethoxybenzene → (R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)aniline

温度

120 °C

Palladium(II) acetate (0.427 g, 1.90 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.906 g, 1.90 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromobenzene (5 g, 19.00 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (4.32 g, 22.80 mmol) and Cesium carbonate (2.281 mL, 28.50 mmol) in toluene (75 mL) at 20°C under nitrogen. The resulting suspension was stirred at 120°C for 72 hours. The reaction mixture was diluted with EtOAc (150mL) and water (150mL) and the biphasic mixture was filtered through celite. The organic layer was seperated and washed sequentially with water (150mL) and saturated brine (150mL). The organic layer was evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford (R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)aniline (4.60 g, 65.1 %) as an orange oil.

ORDレコード

ord-507c2159372a46eb8fb0f4b142612613

出典データセット

750 AstraZeneca ELN dataset

元リンク

出典を表示