HCID 131728983, compound → HCID 131728982, compound

HRID 2428193Notes

Reaction equation

HRID 2428193 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18]CC3C=CC=CC=3)=[CH:14][CH:13]=2)[CH2:10][C@H:9]2[N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:6]1[CH2:7][CH2:8]2)=[O:4]>CO.C1COCC1.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:11]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[CH2:10][C@H:9]2[N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@@H:6]1[CH2:7][CH2:8]2)=[O:4]

Participants

5

Reactant 1

HCID 131728983HCID 131728983, compound

Product 1

HCID 131728982HCID 131728982, compoundYield 97.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Pd(OH)2 on charcoal (20%, 76 mg) was added to a sol. of compound E6 (760 mg, 1.68 mmol) in MeOH (5.00 mL) and THF (5 mL). The mixture was purged with N2, then with H2. The mixture was stirred under an atmosphere of H2 overnight. The mixture was filtered through celite, and the filtrate was evaporated under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (590 mg, 97%) that was used further without purification. LC-MS: tR=0.95 min; ES+: 347.36.

Workup

  1. customThe mixture was purged with N2
  2. filtrationThe mixture was filtered through celite
  3. customthe filtrate was evaporated under reduced pressure
  4. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-b7308e079fe94ddca4930dd7a69e8c7b
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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