(+/-)-trans-3-[4-(benzyloxy)phenyl]-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrrolidine-2,5-dione → (+/-)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(4-hydroxyphenyl)pyrrolidine-2,5-dione

HRID 405898Notes

Reaction equation

HRID 405898 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[C@H:19]([C:20]3[C:30]4=[C:31]5[C:26](=[CH:27][CH:28]=[CH:29]4)[CH2:25][CH2:24][CH2:23][N:22]5[CH:21]=3)[C:18](=[O:32])[NH:17][C:16]2=[O:33])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd]>[C:20]1([C@H:19]2[C@H:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[C:16](=[O:33])[NH:17][C:18]2=[O:32])[C:30]2=[C:31]3[C:26](=[CH:27][CH:28]=[CH:29]2)[CH2:25][CH2:24][CH2:23][N:22]3[CH:21]=1

Participants

4

Reactant 2

HCID 69396599(+/-)-trans-3-[4-(benzyloxy)phenyl]-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrrolidine-2,5-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 69397593(+/-)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(4-hydroxyphenyl)pyrrolidine-2,5-dioneYield 44.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (±)-trans-3-[4-(benzyloxy)phenyl]-4-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)pyrrolidine-2,5-dione (0.2 g) and Pd/C (10% w/w, 0.076 g) was stirred under 1 atmosphere of hydrogen gas overnight. The catalyst was filtered off through a pad of celite and concentrated. The residue was purified by column chromatography on silica gel eluting with 30-40% ethyl acetate in hexane to provide (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(4-hydroxyphenyl)pyrrolidine-2,5-dione 0.07 g as a light yellow solid. Mp 105-107° C.; 1H NMR (acetone-d6) 400 MHz δ: 10.27 (s. 1 H), 8.34 (s, 1 H), 7.17-7.21 (m, 4 H), 6.80-6.91 (m, 4 H), 4.39 (d, J=7.0 Hz, 1 H), 4.22 (d, J=7.0 Hz, 1 H), 4.13 (d, J=5.6 Hz, 2 H), 2.92 (d, J=5.2 Hz, 2 H), 2.15-2.19 (m, 2 H).

Workup

  1. filtrationThe catalyst was filtered off through a pad of celite
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography on silica gel eluting with 30-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d8db5065dc80417e8b48f52859f86b24
Source dataset
uspto-grants-2014_06
Patent number
US08754078B2

Reaction notes

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