Phthalic Anhydride → 1H-Isoindole-1,3(2H)-dione, 2-[(1R)-2-hydroxy-1-phenylethyl]-

Participants

Reaction Conditions

Reaction Steps

To a 2.0-5.0 mL microwave vial was added (R)-2-amino-2-phenylethan-1-ol (1.53 g, 0.0112 mol) and phthalic anhydride (1.65 g, 0.0112 mol). The reaction mixture was capped and heated to 150° C. for 2 minutes in a microwave reactor. The mixture was cooled and diluted with CH3CN (2 mL), recapped and heated in the microwave reactor a second time at 140° C. for 20 minutes. The volatiles were removed under reduced pressure and the resulting solid was suspended in EtOAc (50 mL). The organic layer was washed with 5% NaHCO3 (aq), H2O, and brine, dried with anhydrous MgSO4 and concentrated. The crude residue was purified by flash chromatography (silica gel, eluting with CH3OH in CH2Cl2 (0 to 5%) to yield 2.81 g (94%) of the title compound. LC/MS: m/z (ES+) 268 (M+H)+.

Provenance & Evidence