HCID 66671553, compound → HCID 66671952, compound

HRID 1171152Notes

Reaction equation

HRID 1171152 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]3[C:25]([Cl:26])=[CH:24][C:23]([O:27]CC4C=CC=CC=4)=[CH:22][C:21]=3[Cl:35])[C:15]2=[O:36])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]3[C:25]([Cl:26])=[CH:24][C:23]([OH:27])=[CH:22][C:21]=3[Cl:35])[C:15]2=[O:36])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66671553HCID 66671553, compound

Product 1

HCID 66671952HCID 66671952, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 4-[(R)-3-(4-Benzyloxy-2,6-dichloro-benzyl)-2-oxo-pyrrolidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Preparation 13) (2.2 g, 4.1 mmol) in EtOAc (50 mL) with Palladium Hydroxide on carbon (0.1 g). Purge the solution with Hydrogen and stir the reaction overnight under 1 atm of hydrogen. Filter the reaction through celite to remove the catalyst. Remove the solvent to afford 1.6 g (87%) of desired product. MS (m/e): 441 (M−1).

Workup

  1. customPurge the solution with Hydrogen
  2. customthe reaction overnight under 1 atm of hydrogen
  3. filtrationFilter
  4. customthe reaction through celite
  5. customto remove the catalyst
  6. customRemove the solvent

Sources & evidence

ORD record
ord-27284ff57522436b89ab299861ff64f3
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

Loading…