HCID 178428944, compound → HCID 178429004, compound

HRID 1013811Notes

Reaction equation

HRID 1013811 reaction equation
C([O:8][C:9]1[CH:30]=[C:29]([CH3:31])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:27][CH2:26][C:25]4[C:21](=[CH:22][NH:23][N:24]=4)[CH2:20]3)[C:15]2=[O:28])=[C:11]([CH3:32])[CH:10]=1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:30]=[C:29]([CH3:31])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:27][CH2:26][C:25]4[C:21](=[CH:22][NH:23][N:24]=4)[CH2:20]3)[C:15]2=[O:28])=[C:11]([CH3:32])[CH:10]=1

Participants

4

Reactant 1

HCID 178428944HCID 178428944, compound

Product 1

HCID 178429004HCID 178429004, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Treat a solution of (R)-3-(4-Benzyloxy-2,6-dimethyl-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one (Preparation 64) (1.65 g, 3.8 mmol) in EtOH (20 mL) with Palladium Hydroxide on carbon (1.7 g). Purge the solution with Hydrogen and pressurize to 35 psi. The reaction stirs 2 days at 35 psi of hydrogen. Filter the reaction through celite to remove catalyst. Purify the crude by silica gel column chromatography using CH2Cl2 and 2M Ammonia in MeOH to elute the pure product. Remove the solvent to afford 0.85 g (65%) of desired product. MS (m/e): 340 (M+1).

Workup

  1. customPurge the solution with Hydrogen
  2. filtrationFilter
  3. customthe reaction through celite
  4. customto remove catalyst
  5. customPurify the crude by silica gel column chromatography
  6. washto elute the pure product
  7. customRemove the solvent

Sources & evidence

ORD record
ord-92701c9feddd4cecbbeeb14191410c8d
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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