Water → 4-({4-[(trans)-2-Aminocyclopropyl]phenoxy}methyl)benzonitrile

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Reaction Steps

tert-butyl(trans)-2-{4-[(4-cyanobenzyl)oxy]phenyl}cyclopropylcarbamate (0.31 g, 0.85 mmol) was dissolved in a mixture of 1,4-dioxane/H2SO4 (15 mL, 10:1, v/v) and stirred at room temperature for 45 min. The reaction mixture was poured into water (15 mL), basified by addition of 15 mL of aqueous NaOH (10%) and extracted with EtOAc (2×15 mL); the organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the crude residue was purified by column chromatography on silica gel (0%-3% MeOH/CH2Cl2) to afford 0.19 g of 4-({4-[(trans)-2-aminocyclopropyl]phenoxy}methyl)benzonitrile [Rf=0.2 (5% MeOH/CH2Cl2), beige solid, 85% yield].

Provenance & Evidence