1-benzyl 2-tert-butyl (2S,4R)-5-oxo-4-[(2E)-3-phenyl-2-propenyl]-1,2-pyrrolidinedicarboxylate → tert-butyl (2S,4R)-5-oxo-4-(3-phenylpropyl)-2-pyrrolidinecarboxylate

HRID 481245Notes

Reaction equation

HRID 481245 reaction equation
[O:1]=[C:2]1[N:6](C(OCC2C=CC=CC=2)=O)[C@H:5]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:4][C@H:3]1[CH2:24]/[CH:25]=[CH:26]/[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(O)=O.[Pd]>[O:1]=[C:2]1[NH:6][C@H:5]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:4][C@H:3]1[CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 865875621-benzyl 2-tert-butyl (2S,4R)-5-oxo-4-[(2E)-3-phenyl-2-propenyl]-1,2-pyrrolidinedicarboxylate

Product 1

HCID 86587563tert-butyl (2S,4R)-5-oxo-4-(3-phenylpropyl)-2-pyrrolidinecarboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The protected pyroglutamate 8b (370 mg, 0.850 mmol) was partially dissolved in 1:1 EtOAc/hexanes (20 mL) and 100 □L AcOH. To this mixture, was added 10% Pd-C (50 mg). The mixture was evacuated and flushed with H2 (5×), then stirred under an atmosphere of H2 for 45 min. The reaction mixture was filtered and concentrated to afford 251.4 mg (98%) of 8c.

Workup

  1. customThe mixture was evacuated
  2. customflushed with H2 (5×)
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1993c780254f47e8bc5d6065b7012c21
Source dataset
uspto-grants-2003_11
Patent number
US06653295B2

Reaction notes

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