HCID 68734622, compound → HCID 68734802, compound

HRID 2382198Notes

Reaction equation

HRID 2382198 reaction equation
[C:1]1(/[C:7](/[C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)=[C:8]2/[CH2:9][NH:10][CH2:11][CH2:12]/2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>CO.[Pd]>[C:1]1([CH:7]([C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)[CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 68734622HCID 68734622, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68734802HCID 68734802, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (Z)-3-(phenyl(m-tolyl)methylene)pyrrolidine (4.0 g, 16.1 mmol) in methanol (40 mL) at room temperature was added 10% Pd/C (9.5 g) and the contents were hydrogenated at 50 psi hydrogen atmosphere and at room temperature for 12 h. The reaction mixture was filtered through celite bed and the bed was washed with methanol. The filtrate was concentrated under reduced pressure to afford 3.0 g of 3-(phenyl(m-tolyl)methyl)pyrrolidine.

Workup

  1. filtrationThe reaction mixture was filtered through celite bed
  2. washthe bed was washed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f966a1c6f15d4dff87115635d83c9412
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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