7-amino-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-one → 7-amino-4-(1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 511246Notes

Reaction equation

HRID 511246 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]2[CH2:22][CH2:21][C:16]3([O:20][CH2:19][CH2:18][O:17]3)[CH2:15][CH:14]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2>CCO.[Pd]>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]2[CH2:22][CH2:21][C:16]3([O:20][CH2:19][CH2:18][O:17]3)[CH2:15][CH2:14]2)=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[CH2:7]2

Participants

4

Reactant 1

HCID 672553637-amino-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 672557217-amino-4-(1,4-dioxaspiro[4.5]dec-8-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7-amino-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-2-methyl-2,3-dihydro-1H-isoindol-1-one (1.7 g, 5.7 mmol) in EtOH (100 mL) was added palladium 10% wt on activated carbon (0.60 g, 0.57 mmol). The reaction mixture was evacuated and purged with hydrogen (3×) and stirred over night at rt. The reaction mixture was filtered through a pad of celite and concentrated in vacuo to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.04 (d, J=8.34 Hz, 1H), 6.52 (d, J=8.08 Hz, 1H), 5.85 (s, 2H), 4.34 (s, 2H), 3.86-3.89 (m, 4H), 2.98 (s, 3H), 2.42-2.48 (m, 1H), 1.52-1.80 (m, 8H); MS (ES+): m/z: 303.1516 [MH+]. HPLC: tR=1.21 min (UPLC TOF MS: polar—3 min).

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with hydrogen (3×)
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2da0df9e24f4254906712a8709b9e59
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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