Sodium hydride → (R)-2-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

To a 25 mL vial which contained a suspension of NaH (60% in mineral oil, 30 mg, 0.75 mmol) in DMF (3 mL) was added 2-(4-Hydroxy-phenyl)-isoindole-1,3-dione (105 mg, 0.5 mmol) at 0° C. The mixture was allowed to warm to rt and stir at rt for 30 min then cooled to 0° C. To this reaction mixture was added (R)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (173 mg, 0.5 mmol) at 0° C. The resulting mixture was allowed to warm to rt and stir at rt for 30 min and then was heated to 90° C. and stirred at 90° C. for 16 h. After cooled to it, the mixture was poured into 150 mL ice-water solution and then was extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (3×50 mL), brine (30 mL) and dried over Na2SO4. After concentrated in vacuo, the residue was purified by a column chromatography on silica gel to yield the title product, (120 mg, 55%)

Provenance & Evidence