(S)-1-Benzyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate → HCID 45089984, compound

HRID 1245033Notes

Reaction equation

HRID 1245033 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C:7](=[CH2:9])[CH2:6][N:5]1C(OCC1C=CC=CC=1)=O>[Pd].CO>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][CH:7]([CH3:9])[CH2:6][NH:5]1

Participants

4

Reactant 1

HCID 54190049(S)-1-Benzyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate

Product 1

HCID 45089984HCID 45089984, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

180 mg of 10% palladium on carbon were added to a solution of 1.80 g (6.5 mmol) of (S)-1-benzyloxycarbonyl-4-methylideneproline methyl ester [obtained as described in Preparative Example 8(i)′ above] in 50 ml of methanol, and the resulting mixture was stirred for 2 hours at room temperature under a hydrogen atmosphere. At the end of this time, the reaction mixture was filtered and the filtrate was concentrated by evaporation under reduced pressure to afford 0.93 g (quantitative yield) of the title compound as a pale yellow oil.

Workup

  1. customobtained
  2. filtrationAt the end of this time, the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1e1b1ba5c92247f2ac835f7fad2f4c4e
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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