Ammonium Chloride → 2-(3-Hydroxy-3-phenylcyclopentyl)isoindoline-1,3-dione

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Reaction Steps

A solution of Example 58A (1.00 g, 4.36 mmol) and THF (20 mL) was cooled to <−70° C. and phenylmagnesium chloride (2.40 mL, 4.80 mmol) was added at <−70° C. After 2 hours, saturated aqueous NH4Cl (20 mL) was added and the mixture was extracted with MTBE (50 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was puridifed by flash column chromatography (0-20% EtOAc/hexanes, gradient elution), to provide the title compound (370 mg, 1.20 mmol, 27.6% yield).

Provenance & Evidence