Tetrahydrofuran → HCID 44358869, compound

HRID 1511166Notes

Reaction equation

HRID 1511166 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH:13]=[CH:14][C:15]([NH2:17])=[O:16])=[CH:5][CH:4]=1.C1COCC1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][C:15]([NH2:17])=[O:16])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 66602096HCID 66602096, compound

Product 1

HCID 44358869HCID 44358869, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

0.12 g of 5% Pd/C (50% wet) is added to a solution of the compound obtained in Step A (0.5 g) in a mixture of MeOH (6.5 mL)/THF (6.5 mL). The mixture is purged with nitrogen and then with hydrogen before being heated at 50° C. under atmospheric pressure during 1 hour. The suspension is then filtered over Celite and the filter is washed with a mixture of MeOH (5 mL)/THF (5 mL). The liquors are concentrated under reduced pressure to yield the title product in the form of a solid which is directly engaged in the following step without further purification.

Workup

  1. customThe mixture is purged with nitrogen
  2. filtrationThe suspension is then filtered over Celite
  3. washthe filter is washed with a mixture of MeOH (5 mL)/THF (5 mL)
  4. concentrationThe liquors are concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc38901a3c9a43819ed94453b724384e
Source dataset
uspto-grants-2012_07
Patent number
US08212077B2

Reaction notes

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