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

HRID 9892Notes

Reaction equation

HRID 9892 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.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][CH:7]([CH3:9])[CH2:6][NH:5]1

Participants

5

Reactant 2

HCID 54190049(S)-1-Benzyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 45089984HCID 45089984, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-1-Benzyloxycarbonyl-4-methylideneproline methyl ester (1.80 g (6.5 mmol), prepared as described in 1)) was dissolved in methanol (50 ml). The resulting solution was stirred at room temperature in an atmosphere of hydrogen in the presence of 10% palladium on charcoal (180 mg) for 2 hours. At the end of this time, the reaction mixture was filtered to remove the catalyst and the filtrate was concentrated by evaporation under reduced pressure, to give the title compound (0.93 g) as a pale yellow oil (yield quantitative).

Workup

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

Sources & evidence

ORD record
ord-f51ae708c7b34b70880763ac6b68d07a
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Reaction notes

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