1,4-Cyclohexadiene → HCID 86609514, compound

HRID 495212Notes

Reaction equation

HRID 495212 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])=[C:6]([CH:18]=[O:19])[NH:5][C:4]=1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:2].C1CC=CCC=1>C(O)C.[Pd]>[C:23]([O:22][C:20]([C:4]1[NH:5][C:6]([CH:18]=[O:19])=[C:7]([C:8]([OH:10])=[O:9])[C:3]=1[CH2:1][CH3:2])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 10108979HCID 10108979, compound

Product 1

HCID 86609514HCID 86609514, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-benzyl 2-tert-butyl 3-ethyl-5-formyl-1H-pyrrole-2,4-dicarboxylate (1.316 g, 3.682 mmol) in ethanol (15.0 mL) was added 10% palladium on carbon (1.300 g, 3.68 mmol) and 1,4-cyclohexadiene (3.50 mL, 36.82 mmol). The reaction was stirred under N2 for 2 h prior to filtration through a pad of Celite. The filtrate was washed with 50 mL of ethyl acetate and the combined organics concentrated in vacuo. The resultant residue was purified by preparative reverse phase HPLC. Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CD3OD) δ 10.23 (s, 1H); 3.10 (q, J=7.3 Hz, 2H); 1.61 (s, 9H); 1.16 (t, J=7.3 Hz, 3H). HRMS (ES) exact mass calculated for C13H17NNaO5 (M+Na+): 290.1001. Found 290.1001.

Workup

  1. filtrationto filtration through a pad of Celite
  2. washThe filtrate was washed with 50 mL of ethyl acetate
  3. concentrationthe combined organics concentrated in vacuo
  4. customThe resultant residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-4cc38575f28c49b08b2a83cfaabc9766
Source dataset
uspto-grants-2009_05
Patent number
US07538231B2

Reaction notes

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