HCID 86725304, compound → HCID 86725303, compound

HRID 925188Notes

Reaction equation

HRID 925188 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:21][CH2:20][C:10]2[C:11]3[C:12](=[O:19])[CH2:13][CH2:14][C:15]=3[C:16](I)=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>CCO.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:21][CH2:20][C:10]2[C:11]3[C:12](=[O:19])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 86725304HCID 86725304, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86725303HCID 86725303, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a 500 ml Parr bottle, Intermediate 1 (11 g, 27.56 mmol) was added, followed by 5% Pd—C (700 mg) in EtOH (200 ml). The mixture was shaken over 50 psi hydrogen for 16 hours. The contents were filtered through celite and solvent evaporated in vacuo. The remaining residue was purified by silica-gel chromatography (gradient elution: 0 to 40% EtOAc in hexane) to give the title product as a white solid (6.1 g). 1H NMR (300 MHz, CDCl3) δ 7.31 (d, J=7.8 Hz, 1H); 7.22 (d, J=7.8 Hz, 1H); 4.16 (q, J=6.9 Hz, 2H); 3.62-3.60 (m, 6 μl); 3.05-2.96 (m, 4 μl); 2.70-2.66 (m, 2H); 1.27 (t, J=6.9 Hz, 3H; MS: ESI (positive): 274 (M+H).

Workup

  1. filtrationThe contents were filtered through celite and solvent
  2. customevaporated in vacuo
  3. customThe remaining residue was purified by silica-gel chromatography (gradient elution: 0 to 40% EtOAc in hexane)

Sources & evidence

ORD record
ord-81a7d09514ff445cabb941b8e88a8b79
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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