反应详情

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).

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