HCID 86723606, compound → HCID 86723605, compound

HRID 590669Notes

Reaction equation

HRID 590669 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:6]=1[CH3:7]>CCO.[Pt]>[CH3:1][C@@H:2]1[C@H:6]([CH3:7])[N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[C@H:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:3]1

Participants

4

Reactant 1

HCID 86723606HCID 86723606, compound

Product 1

HCID 86723605HCID 86723605, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-tert-butyl 2-ethyl 4,5-dimethyl-1H-pyrrole-1,2-dicarboxylate (4.016 g, 15.02 mmol) in EtOH (100 mL) was added Platinum on carbon (5%, 0.58 g). The slurry was stirred under an atmosphere of hydrogen (1 atm) for 3 days. The slurry was filtered through celite and washed with MeOH. The filtrate was concentrated and the crude was purified by column chromatography (SiO2, 5-10-20% EtOAc/Hexanes) to provide rel-(2S,4S,5S)-1-tert-butyl 2-ethyl 4,5-dimethylpyrrolidine-1,2-dicarboxylate.

Workup

  1. filtrationThe slurry was filtered through celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated
  4. customthe crude was purified by column chromatography (SiO2, 5-10-20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-b54879ca38a744ebb324c04b142ffd59
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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