Lithium triethylborohydride → benzyl 5-(hydroxymethyl)-6-iodo-1,3-dihydro-2H-isoindole-2-carboxylate

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Reaction Conditions

Reaction Steps

To a solution of 2-benzyl 5-methyl 6-iodo-1,3-dihydro-2H-isoindole-2,5-dicarboxylate (104 mg, 0.238 mmol) in THF (5 mL) at −78° C. under N2, was added dropwise 1N Super Hydride in THF (476 uL, 0.476 mmol). The mixture was stirred at −78° C. for 2 h. The reaction mixture was quenched with 1N HCl. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to provide benzyl 5-(hydroxymethyl)-6-iodo-1,3-dihydro-2H-isoindole-2-carboxylate. LCMS calc.=432.0; found=431.9 (M+Na)+. 1H NMR (500 MHz, CDCl3): δ 7.76-7.70 (2 s, 1H); 7.45-7.35 (m, 6H); 5.24 (s, 2H); 4.76-4.67 (m, 4H); 2.18 (br s, 1H).

Provenance & Evidence