Methanol → 5-Hydroxy-2-(2-hydroxyethyl)-2,3-dihydro-1H-isoindol-1-one

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Reaction Steps

A mixture of 5-methoxy-2-(2-methoxy-ethyl)-2,3-dihydro-isoindol-1-one (150 mg, 0.68 mmol) and boron tribromide (1 M in CH2Cl2, 1.4 mL, 1.36 mmol) in CH2Cl2 (8 mL) at −78° C. was stirred for 16 h at RT. The mixture was then cooled to −78° C. and MeOH (25 mL) was added. After 1 h at −78° C. the mixture was evaporated and the residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 98:2 to 90:10) to afford the title product (42 mg, 32%) as a light orange solid. MS m/e=193.3 (M+).

Provenance & Evidence