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)-

HRID 2354597Notes

Reaction equation

HRID 2354597 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]5[O:22][CH2:21][O:20][C:18]5=4)[CH:13]=[C:12]4[C:23](=[O:37])[N:24]([CH2:26][CH2:27][CH2:28][O:29]CC5C=CC=CC=5)[CH2:25][C:11]=34)=[CH:9][C:4]=2[O:3][CH2:2]1.[H][H]>C1COCC1.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]5[O:22][CH2:21][O:20][C:18]5=4)[CH:13]=[C:12]4[C:23](=[O:37])[N:24]([CH2:26][CH2:27][CH2:28][OH:29])[CH2:25][C:11]=34)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 52737947H-1,3-Benzodioxolo[4,5-f]isoindol-7-one, 10-(1,3-benzodioxol-5-yl)-8,9-dihydro-8-[3-(phenylmethoxy)propyl]-HCID 178418361HCID 178418361, compound

Product 1

HCID 52737957H-1,3-Benzodioxolo[4,5-f]isoindol-7-one, 10-(1,3-benzodioxol-5-yl)-8,9-dihydro-8-(3-hydroxypropyl)-Yield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  1. customThe Pd/C was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-aac57d985d124546ab186ba9f6ec7585
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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