HCID 57179453, compound → HCID 54531199, compound

HRID 1954617Notes

Reaction equation

HRID 1954617 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:10]2[CH2:14][N:13]([C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[C:12](=[O:23])[CH:11]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>C(O)C.[Pt]=O>[CH2:1]([O:3][C:4]([C:6]1([CH:10]2[CH2:14][N:13]([C@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[C:12](=[O:23])[CH2:11]2)[CH2:7][CH2:8][CH2:9]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 57179453HCID 57179453, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54531199HCID 54531199, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

4-(1-Ethoxycarbonylcyclobutyl)-1-[(S)-1-phenylethyl]-3-pyrrolin-2-one (9.57 g, 31 mmol) was dissolved in ethanol (150 ml), and the solution was mixed with platinum oxide (230 mg) and stirred for 18 hours in a hydrogen atmosphere. After completing the reaction, the reaction solution was filtered and concentrated, and the resulting residue was applied three times to a silica gel chromatography column and eluted with an eluant of n-hexane:ethyl acetate=1:1, to thereby obtain optical isomer A (2.3 g, 24%) and optical isomer B (7.1 g, 74%) of the title compound each in an oily form.

Workup

  1. customthe reaction
  2. filtrationthe reaction solution was filtered
  3. concentrationconcentrated
  4. washeluted with an eluant of n-hexane

Sources & evidence

ORD record
ord-ac3df2e7edda4f37aa80f40125ada162
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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