Tetrahydrofuran ethanol → HCID 57974910, compound

HRID 1865075Notes

Reaction equation

HRID 1865075 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:29])[C:8]([CH2:27][CH3:28])=[C:9]([C:25]#[N:26])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[CH:13][CH:12]=1)=[O:5])[CH3:2].CCO.C1COCC1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:29])[C:8]([CH2:27][CH3:28])=[C:9]([C:25]#[N:26])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 21873804Tetrahydrofuran ethanolHCID 69020301HCID 69020301, compound

Product 1

HCID 57974910HCID 57974910, compoundYield 196.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 20% Pd(OH)2/C (6.95 g) and 3-(4-benzyloxy-phenyl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (23.173 g, 59.65 mmol, prepared in example E-80a or E-80b) in a 1/2 EtOH/THF solution (300 mL) is placed under 50 PSI of H2 at room temperature for 3.5 hours. The reaction mixture is combined with another reaction mixture of the same scale, and the combined reaction mixtures are filtered through Hyflo, washing with EtOAc. The filtrate is concentrated in vacuo to afford a white residue. The white residue is dissolved in a minimal amount of EtOAc, then treated with excess hexanes, causing a precipitate to form. The resulting white solid is recovered by vacuum filtration, washing with hexanes and drying under vacuum to afford the title compound (35.01 g, 98% yield) as a white solid: 1H NMR (500 MHz; CDCl3) δ 7.23 (d, 2H), 6.83 (d, 2H), 5.46 (s, 1H), 4.11 (q, 2H), 3.87 (s, 3H), 2.84 (q, 2H), 1.30 (t, 3H), 1.06 (t, 3H); MS(ES): m/z 299.1 (M++H), 297.1 (M−H−). Anal. Calcd. For C17H18N2O3: C, 68.44; H, 6.08; N, 9.38. Found C, 68.18, H, 6.06; N, 9.34.

Workup

  1. customis placed under 50 PSI of H2 at room temperature for 3.5 hours
  2. additionThe reaction mixture is combined with another reaction mixture of the same scale
  3. customthe combined reaction mixtures
  4. filtrationare filtered through Hyflo
  5. washwashing with EtOAc
  6. concentrationThe filtrate is concentrated in vacuo
  7. customto afford a white residue
  8. customto form
  9. filtrationThe resulting white solid is recovered by vacuum filtration
  10. washwashing with hexanes
  11. customdrying under vacuum

Sources & evidence

ORD record
ord-5f7c0535285f47cebc79599a82516fd0
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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