Ethanol → HCID 69021586, compound

HRID 1865069Notes

Reaction equation

HRID 1865069 reaction equation
C(O)C.[CH2:4]([O:6][C:7]([C:9]1[N:10]([CH3:30])[CH:11]=[C:12]([C:28]#[N:29])[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20]CC2C=CC=CC=2)=[CH:16][CH:15]=1)=[O:8])[CH3:5].[H][H]>[OH-].[OH-].[Pd+2].C1COCC1>[CH2:4]([O:6][C:7]([C:9]1[N:10]([CH3:30])[CH:11]=[C:12]([C:28]#[N:29])[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[O:8])[CH3:5]

Participants

6

Reactant 3

HCID 702EthanolHCID 69022513HCID 69022513, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69021586HCID 69021586, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Add a 1:2 ethanol:THF mixture to 20% palladium hydroxide on carbon (catalytic, 29.4 g) followed by 3-(4-benzyloxy-phenyl)-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (97.93 g, 0.271 mol, prepared in examples E-6a or E-6b). Subject the reaction to 344.74 kPa (50 psi) of hydrogen gas. After 18 hours, filter and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexanes to provide the title compound. Mass spectrum (m/e): 271.1 (M+1).

Workup

  1. filtrationfilter
  2. concentrationconcentrate under reduced pressure
  3. customPurify the residue by flash chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-6974506fbca3466caea2f2391a5c060a
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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