Diisopropylamine → Methyl 2-[4-(t-butoxycarbonylaminomethyl)-benzyl]-tetrahydro-2-furancarboxylate

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Reaction Steps

To a solution of diisopropylamine in 10 ml of tetrahydrofuran was added 5.5 ml of 1.6 M solution of n-butyllithium in hexane at −78° C. under an atmosphere of nitrogen gas. After stirring for 30 minutes, a solution of 1.17 g of methyl tetrahydro-2-furancarboxylate in 10 ml of tetrahydrofuran was added dropwise. After stirring for further 30 minutes, a solution of 1.20 g of t-butyl N-[4-(bromomethyl)benzyl]carbamate in 20 ml of tetrahydrofuran was added dropwise, and the mixture was stirred at −78° C. for 3 hours. 50 ml of saturated aqueous ammonium chloride, 200 ml of ethyl acetate and 100 ml of water were added, and the organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography, to give 0.961 g of the title compound.

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