Ethanol → HCID 178472342, compound

Participants

Reaction Steps

A solution of ethyl 4-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)cyclohex-3-ene-1-carboxylate (1.03 g, 2.99 mmol) in EtOH (2.6 mL, 45 mmol) was charged with palladium 10% wt on activated carbon (0.1:0.9, Palladium:Carbon, 0.11 g, 0.10 mmol). The reaction mixture was evacuated and purged with hydrogen gas (3×). The reaction mixture was allowed to stir under hydrogen gas at rt for 16 h. The reaction mixture was filtered through a pad of celite. The filtrate was collected and then concentrated in vacuo to oil. The two isomers were resolved by SFC purification to afford 544 mg (58% yield) of the cis and 232 mg (25% yield) of the trans title compounds. Cis: 1H NMR (400 MHz, Methanol-d) δ ppm 7.06 (d, J=8.34 Hz, 1H), 6.61 (d, J=8.34 Hz, 1H), 4.37 (s, 2H), 4.20 (q, J=7.07 Hz, 2H), 3.11 (s, 3H), 2.72 (d, J=2.53 Hz, 1H), 2.46-2.56 (m, 1H), 2.22-2.29 (m, 2H), 1.60-1.75 (m, 6H), 1.29 (t, 3H). MS (ES+): m/z 317.14/319.18 (100/15) [MH+]. HPLC: tR=1.41 min (Micromass TOF: polar—3 min). Trans: 1H NMR (400 MHz, Methanol-d) δ ppm 7.15 (d, J=8.34 Hz, 1H), 6.62 (d, J=8.34 Hz, 1H), 4.38 (s, 2H), 4.13 (q, J=7.16 Hz, 2H), 3.11 (s, 3H), 2.34-2.54 (m, 2H), 2.04-2.11 (m, 2H), 1.82-1.92 (m, 2H), 1.48-1.64 (m, 4H), 1.26 (t, 3H). MS (ES+): m/z 317.15/319.16 (100/7) [MH+]. HPLC: tR=1.38 min (UPLC TOF, polar—3 min).

Provenance & Evidence