N-(9-Fluorenylmethoxycarbonyloxy)succinimide → 173911-21-2

Participants

Reaction Steps

A solution of 4-(3-carboxyphenyl)benzylamine hydrochloride (20 g, 0.075 mol) in 10% Na2CO3 (350 mL) and dioxane (100 mL) was cooled to 0° C. with stirring. A solution of Fmoc-OSu (30.7 g, 0.091 mol) in dioxane (100 mL) was added in one portion and the reaction mixture was stirred at RT for 3 h. Acidified with 1.5 N aqueous solution of HCl and extracted with EtOAc (3×400 mL). The organic layer was washed with water (3×500 mL), brine dried over Na2SO4 and concentrated, purification by column chromatography using dichloromethane/methanol (9:1) to give N-Fmoc-4-(3-carboxyphenyl)benzylamine (16 g). This was further purified by recrystallization from THF/PetEther gave the title pure product (8 g).

Provenance & Evidence