HCID 68429571, compound → HCID 68430118, compound

HRID 2191249Notes

Reaction equation

HRID 2191249 reaction equation
C([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[C:20]([O:19][C:17]1[CH:16]=[CH:15][C:13]2[CH2:14][NH:8][CH2:9][CH2:10][O:11][C:12]=2[N:18]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 68429571HCID 68429571, compound

Product 1

HCID 68430118HCID 68430118, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of the compound obtained in step 1 (0.81 g), 20% Pd(OH)2/C (0.081 g) and methanol (10 mL) was stirred at 40° C. for 2 days under a hydrogen atmosphere. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (solvent gradient; 40→100% ethyl acetate/hexane) to give the title compound (0.16 g, 57%) as a colorless oil.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (solvent gradient; 40→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2423e133a1a04be5a5a84b0be7e81885
Source dataset
uspto-grants-2012_12
Patent number
US08329687B2

Reaction notes

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