HCID 68295261, compound → HCID 68295055, compound

HRID 572526Notes

Reaction equation

HRID 572526 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH3:20])[C:10]=1[CH:21]([CH2:25][CH:26]=[CH2:27])[C:22]([OH:24])=[O:23]>C(OCC)(=O)C.[Pt](=O)=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[N:11]([CH3:20])[C:10]=1[CH:21]([CH2:25][CH2:26][CH3:27])[C:22]([OH:24])=[O:23]

Participants

4

Reactant 1

HCID 68295261HCID 68295261, compound

Product 1

HCID 68295055HCID 68295055, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-(2,4-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)pent-4-enoic acid (69 mg, 0.162 mmol,) in ethyl acetate (2 mL) was treated with platinum(IV) oxide (8.12 mg, 0.036 mmol) and the mixture was stirred at room temperature under an atmosphere of H2 for 1 hour. The mixture was filtered and the filtrate was purified by reverse phase hplc afford the title compound (31 mg, 52%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.45-8.52 (m, 1 H) 7.43-7.54 (m, 2 H) 7.07-7.23 (m, 2 H) 6.97-7.03 (m, 1 H) 6.81-6.92 (m, 1 H) 3.79-3.97 (m, 1 H) 3.59 (s, 3 H) 2.42 (s, 3 H) 1.94-2.10 (m, 3 H) 1.54-1.74 (m, 2 H) 1.19-1.30 (m, 2 H) 0.72-0.88 (m, 3 H). LC/MS (m/z) ES+=364 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified by reverse phase hplc

Sources & evidence

ORD record
ord-8dd5ef4a2b55438a994bcd972a201a0d
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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