HCID 58100142, compound → (4-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]phenyl}butyl)carbamic acid benzyl ester

HRID 1696850Notes

Reaction equation

HRID 1696850 reaction equation
[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[C:22][CH2:23][CH2:24][N:25]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:35])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[OH-].[OH-].[Pd+2]>[CH2:1]([O:8][C:9](=[O:36])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[C:26](=[O:35])[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]2=[O:34])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58100142HCID 58100142, compound

Product 1

HCID 66860915(4-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]phenyl}butyl)carbamic acid benzyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension containing 58 (6.0 g, 12.59 mmol) and palladium dihydroxide (20% Pd(OH)2 on carbon, 50% wet, 3.0 g, 21.43 mmol) dissolved in anhydrous tetrahydrofuran 75 mL) was bubbled with nitrogen for 20 min. The reaction mixture was vacuumed, then charged with H2 gas (45 psi), and allowed to stir at rt for 24 h. The solution was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the desired product 59 (4.88 g, 80%) as a thick, brown oil: 1H NMR (500 MHz, CDCl3) δ 7.85 (dd, 2H), 7.74 (dd, 2H), 7.35-728 (m, 6H), 7.06 (d, 4H), 3.70 (t, 2H), 3.19 (t, 2H), 2.63-2.56 (m, 4H), 2.00 (d, 2H), 1.73-1.50 (m, 8H); m/z (ESI) 485 [C30H32N2O4+H]+.

Workup

  1. customwas bubbled with nitrogen for 20 min
  2. additioncharged with H2 gas (45 psi)
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resulting residue was purified by column chromatography
  6. washeluting with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-01511e8a109847278242ff904fd3d2bc
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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