Benzyl chloroformate → Isoindoline

Participants

Reaction Steps

To a solution of 1-(2-allyloxy-5-chloro-phenyl)-5-fluoro-2-(2-methyl-propane-2-sulfinyl)-2,3-dihydro-1H-isoindole (230 mg, 0.56 mmol, 1.0 eq.) in MeOH (10 mL), 4M HCl in dioxane (2 mL) was added. The mixture was stirred at r.t. for 2 hours. The reaction mixture was concentrated in vacuo. To a solution of the residue and DIPEA (0.30 mL, 1.69 mmol, 3.0 eq.) in DCM (10 mL), benzyl chloroformate (0.10 mL, 0.68 mmol, 1.2 eq.) was added. The mixture was stirred at r.t. for 4 hours. The reaction mixture was diluted with 1M aq. citric acid soln. (10 mL). The layers were separated. The aq. phase was extracted with DCM (2×10 mL). The comb. org. phases were washed with sat. aq. NaCl soln. (1×10 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo to give the desired isoindoline.

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