3-Chlorophenol → (2S,4S)-4-(3-chloro-phenoxymethyl)-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

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Reaction Steps

To a solution of 4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester (Preparation 45, 132 mg, 0.44 mmol), triphenylphosphine (172 mg, 0.66 mmol) and 3-chlorophenol (0.069 ml, 0.66 mmol) in tetrahydrofuran (5 ml) at 0° C. under a nitrogen atmosphere was added diisopropylazodicarboxylate (0.129 ml; 0.66 mmol) dropwise and allowed to stir to room temperature over 18 hours. The solvent was removed under reduced pressure and the residue purified by chromatography on silica gel, eluting with 10% ethyl acetate/heptane to give the title compound as a colourless gum (66 mg, 37%).

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