HCID 10982168, compound → HCID 10881328, compound

HRID 2306174Notes

Reaction equation

HRID 2306174 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][N:13]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14]1=[O:26])C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[C:22]([O:21][C:19]([NH:18][C@@H:15]1[CH2:16][CH2:17][N:13]([CH2:12][C:11]2[CH:27]=[CH:28][CH:29]=[C:9]([OH:8])[CH:10]=2)[C:14]1=[O:26])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 1

HCID 10982168HCID 10982168, compound

Product 1

HCID 10881328HCID 10881328, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-1-(3-benzyloxybenzyl)-3-(tert-butoxycarbonylamino)-2-oxopyrrolidine, as described above in Step L, (500 mg, 1.26 mmol) in EtOH (75 mL) was added 20% Pd(OH)2 on carbon (75 mg) and the reaction mixture was stirred under an atmosphere of hydrogen (ca. 1 atm) at ambient temperature for 18 hours. The mixture was filtered through a pad of celite, washing with EtOH, and the filtrate was concentrated in vacuo to give a crude product. This was purified by flash column chromatography on silica, eluting with CHCl3—3% MeOH—0.3% NH4OH, to yield the titled product as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing with EtOH
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a crude product
  5. customThis was purified by flash column chromatography on silica
  6. washeluting with CHCl3—3% MeOH—0.3% NH4OH

Sources & evidence

ORD record
ord-d6f22623f3504fb18e677be26f7a2fbf
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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