4-(4-Ethoxycyclohex-1-enyl)-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one → HCID 178468154, compound

HRID 511390Notes

Reaction equation

HRID 511390 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:9][CH2:8][C:7]([C:10]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]3[C:11]=2[CH2:12][N:13]([CH3:23])[C:14]3=[O:22])=[CH:6][CH2:5]1)[CH3:2]>[Pd].C(O)C>[NH2:19][C:16]1[CH:17]=[CH:18][C:10]([C@H:7]2[CH2:8][CH2:9][C@H:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6]2)=[C:11]2[C:15]=1[C:14](=[O:22])[N:13]([CH3:23])[CH2:12]2

Participants

4

Reactant 1

HCID 672529874-(4-Ethoxycyclohex-1-enyl)-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one2×

Product 1

HCID 178468154HCID 178468154, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on charcoal (10%) (50 mg) was cautiously added to a hydrogenation flask containing a solution of 4-(4-ethoxycyclohex-1-enyl)-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one (Compound 166C, 300 mg, 0.78 mmol) in ethanol (30 mL) and this mixture was hydrogenated at 40 psi for 24 hrs. The mixture was filtered and concentrated to a residue which was purified by flash column chromatography (MeOH:DCM 0.5:99.5) to separate the cis and trans isomers. Compound 166A, the cis isomer eluted first: 90 mg: 1H NMR (CDCl3, 500 MHz): 1.22 (t, 3H, J=7.5 Hz), 1.41-1.6 (m, 2H), 1.82 (q, 2H), 2.1 (m, 2H) 2.40 (m, 1H) 3.15 (s, 3H), 3.45 (q, 2H, J=7.5 Hz), 3.62 (s, 1H), 4.36 (s, 2H), 5.08 (s, 2H), 6.6 (d, 1H, J=8 Hz), 7.18 (d, 1H, J=8 Hz). Compound 166B, the trans isomer, eluted after: 50 mg: 1H NMR (CDCl3, 500 MHz): 1.22 (t, 3H, J=7.5 Hz), 1.28 (q, 2H), 1.38 (q, 2H), 1.82 (d, 2H) 2.2 (d, 2H) 2.40 (m, 1H) 3.18 (s, 3H), 3.38 (m, 1H), 3.6 (q, 2H, J=7.5 Hz), 4.38 (s, 2H), 5.1 (s, 2H), 6.6 (d, 1H, J=8 Hz), 7.18 (d, 1H, J=8 Hz).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated to a residue which
  3. customwas purified by flash column chromatography (MeOH:DCM 0.5:99.5)
  4. customto separate the cis and trans isomers
  5. washCompound 166A, the cis isomer eluted first
  6. washCompound 166B, the trans isomer, eluted after: 50 mg

Sources & evidence

ORD record
ord-344abeb33c4a42459760192db465fcfb
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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