HCID 67423254, compound → HCID 46214030, compound

HRID 880716Notes

Reaction equation

HRID 880716 reaction equation
[CH:1]1([NH:7][C:8]([N:10]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21]CC4C=CC=CC=4)=[CH:17][C:16]=3[O:29]CC3C=CC=CC=3)[CH2:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.C(OCC)(=O)C.[Pd]>[CH:1]1([NH:7][C:8]([N:10]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=3[OH:29])[CH2:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 67423254HCID 67423254, compound

Product 1

HCID 46214030HCID 46214030, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 25 ml round-bottomed flask, 0.23 g of 3-(2,4-bis(benzyloxy)phenyl)pyrrolidine-1-carboxylic acid cyclohexylamide is dissolved in 4 ml of methanol in the presence of 3 ml of ethyl acetate and of 0.1 g of palladium-on-charcoal at 10%. The reaction mixture is stirred for 18 hours under a hydrogen atmosphere. The reaction mixture is filtered and the residue is then chromatographed on silica gel (7/3 heptane/ethyl acetate). 0.095 g of 3-(2,4-dihydroxyphenyl)pyrrolidine-1-carboxylic acid cyclohexylamide is obtained. Yield=100%.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe residue is then chromatographed on silica gel (7/3 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-4f8f77a44db54ebd9d65938322854b3b
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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