Ethanol → HCID 178472342, compound

HRID 511240Notes

Reaction equation

HRID 511240 reaction equation
[CH3:1][N:2]1[CH2:10][C:9]2[C:4](=[C:5]([N+:22]([O-])=O)[CH:6]=[CH:7][C:8]=2[C:11]2[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH:12]=2)[C:3]1=[O:25].CCO>[Pd]>[NH2:22][C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[CH2:12][CH2:13][C@H:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:16]2)=[C:9]2[C:4]=1[C:3](=[O:25])[N:2]([CH3:1])[CH2:10]2

Participants

4

Reactant 2

HCID 702EthanolHCID 67253669ethyl 4-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)cyclohex-3-ene-1-carboxylate

Product 1

HCID 178472342HCID 178472342, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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, 1 H), 6.61 (d, J=8.34 Hz, 1 H), 4.37 (s, 2 H), 4.20 (q, J=7.07 Hz, 2 H), 3.11 (s, 3 H), 2.72 (d, J=2.53 Hz, 1 H), 2.46-2.56 (m, 1 H), 2.22-2.29 (m, 2 H), 1.60-1.75 (m, 6 H), 1.29 (t, 3 H). 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, 1 H), 6.62 (d, J=8.34 Hz, 1 H), 4.38 (s, 2 H), 4.13 (q, J=7.16 Hz, 2 H), 3.11 (s, 3 H), 2.34-2.54 (m, 2 H), 2.04-2.11 (m, 2 H), 1.82-1.92 (m, 2 H), 1.48-1.64 (m, 4 H), 1.26 (t, 3 H). MS (ES+): m/z 317.15/319.16 (100/7) [MH+]. HPLC: tR=1.38 min (UPLC TOF, polar—3 min).

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with hydrogen gas (3×)
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. customThe filtrate was collected
  5. concentrationconcentrated in vacuo to oil
  6. customThe two isomers were resolved by SFC purification
  7. customto afford 544 mg (58% yield) of the cis and 232 mg (25% yield) of the trans title compounds
  8. customHPLC: tR=1.41 min (Micromass TOF: polar—3 min)
  9. customHPLC: tR=1.38 min (UPLC TOF, polar—3 min)

Sources & evidence

ORD record
ord-5dd32435076548e0bfe098d802ce058d
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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