7H-1,3-Benzodioxolo[4,5-f]isoindol-7-one, 10-(1,3-benzodioxol-5-yl)-8,9-dihydro-8-[3-(phenylmethoxy)propyl]- → 7H-1,3-Benzodioxolo[4,5-f]isoindol-7-one, 10-(1,3-benzodioxol-5-yl)-8,9-dihydro-8-(3-hydroxypropyl)-

Participants

Reaction Steps

The mixture of 20 (16 mg, 0.032 mmol) and 10% Pd/C (4 mg) in dry THF (3 mL) was stirred for 20 h at room temperature under 1 atm of hydrogen. The Pd/C was removed by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using CH2Cl2/acetone (3:1 to 2:1, v/v) to yield 21 (9 mg, 69%) as a white solid. mp 213-215° C.; 1H NMR (CDCl3) δ 8.31 (s, 1H, H4), 7.67 (d, 1H, H5, J=8.4 Hz), 7.28 (d, 1H, H6, J=8.4 Hz), 6.82-6.92 (m, 3H, H2′+H5′+H6′), 6.07 (AB, 2H, 3′,4′-OCH2O—, Δδ=8.7 Hz, J=1.2 Hz), 5.93 (AB, 2H, 7,8-OCH2O—, Δδ=4.8 Hz, J=1.2 Hz), 4.28 (q, 2H, lactam-CH2—, J=4.8 Hz), 3.77 (t, 2H, NCH2(CH2)2OH, J=4.8 Hz), 3.59 (t, 2H, N(CH2)2CH2OH, J=4.8 Hz), 2.65 (br s, 1H, OH), 1.81 (quintet, 2H, NCH2CH2CH2OH, J=4.8 Hz); MS (EI) m/z 405 [M]+.

Provenance & Evidence